The Kentucky Derby Presented by Woodford Reserve and Super Bowl are uniquely and indelibly etched into the fabric of American culture. One dates back to 1875. The other found its footing in the 1966 season with the first game being played on Jan. 15, 1967. One owns a Saturday, the other a Sunday. They take place roughly three months apart: The Super Bowl now falls in mid-February, while the Kentucky Derby has been run on the first Saturday in May since 1946 – with one exception. In 2020, the race was postponed until the first Saturday in September due to the COVID-19 pandemic.

Both events are must-see television. Last year’s Super Bowl drew a television audience of 99.18 million, while the 2022 Kentucky Derby  was watched by 16 million viewers. 

Both events also represent sports-betting extravaganzas. In 2022, more than $179 million was legally wagered on the Super Bowl (with more than $5 billion estimated illegally). Coincidentally, an equal $179 million also was legally placed on pari-mutuel wagers on the 148^th running of the Kentucky Derby.

In addition to the horse race and the football game, several traditions play a significant role in the atmosphere surrounding each event. 

At the Kentucky Derby, the mint julep is the traditional beverage of the race, the fashion-forward hat scene and contrast between Millionaires Row and the raucous infield is a highlight, and the awarding of the lush blanket of more than 450 red roses to the Kentucky Derby winner each year caps the day. 

The Super Bowl traditions include betting on the coin-toss and a host of other fun and engaging prop bets; watching the halftime entertainment performance from a high-profile, star musician, band and/or rapper; taking part in the living room tailgate party where chicken wings, chips and salsa, and beer are consumed at record levels; and finally not skipping the $5 million commercials so you can see the latest and greatest from an array of brand advertisers looking to sway a captive audience.

But can the result of the Kentucky Derby be used to help predict the Super Bowl winner? 

We took a look at the results, comparing the Derby winner with the Super Bowl winner for each respective year/Super Bowl and, in more than a few cases, noted interesting and coincidental links, foreshadowing opportunities, hunches, and more. 

Will 2023 produce one of those Super Bowls where the previous Kentucky Derby result just might foreshadow the outcome?

Year/Super Bowl — Kentucky Derby Winner — Super Bowl Champion

1966/1967 — Kauai King — Green Bay Packers    

Favorites ruled the day in both: The Derby favorite, Kauai King (paid $6.80 on a $2 bet), and the Super Bowl favorite, the Green Bay Packers, both took care of business. The Packers easily dispatched the overmatched Kansas City Chiefs 35-10.

1967/1968 — Proud Clarion — Green Bay Packers  

Proud Clarion was given little consideration and was sent off by bettors at odds of 30.10-1. A large payday awaited those who heeded the call to back the longshot.

The Packers, on the other hand, were the overwhelming favorite to repeat. Again, the Packers never trailed and cruised to a 33-14 victory, this time over the Oakland Raiders.

1968/1969 — Forward Pass — New York Jets

If you played this hunch bet from the Derby winner you might have scored on Super Bowl III.

Forward Pass, the favorite going into the race, crossed the finish line in second but was the first horse in the history of the Kentucky Derby to have been declared the winner as the result of a disqualification after Dancer’s Image subsequently was found to have used a prohibited medication.

The forward pass certainly played a key role in Super Bowl III. Joe Namath, who famously made an appearance three days before the Super Bowl at the Miami Touchdown Club and personally guaranteed a Jets victory, completed 17 out of 28 passes for 206 yards, and was named the Super Bowl’s most valuable player as his skillful forward passes propelled the Jets to the epic upset. His counterpart, Colts quarterback Earl Morrall, threw three interceptions before being replaced by Johnny Unitas.

1969/1970 — Majestic Prince — Kansas City Chiefs        

The 1969 Derby had a very strong field that deterred entries, and thus only eight horses went to the starting gate, with Majestic Prince set as the 7-5 betting favorite.

But if you played that hunch forward in Super Bowl IV and threw your money behind the Super Bowl favorite Vikings, you lost. The Kansas City Chiefs entered Super Bowl IV as 12 to 13½-point underdogs but soundly defeated the Minnesota Vikings 23-7. 

1970/1971 — Dust Commander — Baltimore Colts

Hunter S. Thompson’s seminal 1970 essay “The Kentucky Derby is Decadent and Depraved” detailed the running of that year’s Derby, which was won by Dust Commander, who paid $32.60 on a $2 bet.

Super Bowl V is sometimes called the “Blunder Bowl,” because it was filled with poor play, a missed PAT, penalties, turnovers, and officiating miscues. The two teams combined for a Super Bowl-record 11 turnovers, with five in the fourth quarter. The Colts (+2 ½ points) defeated the favored Cowboys by the score of 16-13 on a field goal with five seconds left in the game.

1971/1972 — Canonero II — Dallas Cowboys

Canonero II, a bay colt who was born with a noticeably crooked foreleg, was dismissed as a horse that did not belong in such elite company. Yet, in the Derby’s 20-horse field, Canonero II shocked everyone by rallying from 18th to storm past the competition, easily winning the race by  3 ¾ lengths.

This was the last Super Bowl to be blacked out in the TV market in which the game was played. Dallas, in its second Super Bowl appearance, entered the game with a reputation of not being able to win big games. But like Canonero II, the Cowboys (six-point favorites) vanquished their doubters with a decisive 24-3 win over the Miami Dolphins.

1972/1973 — Riva Ridge — Miami Dolphins

Often remembered simply as a stablemate of Secretariat, Riva Ridge was a successful racehorse in his own right, winning 17 of his 30 starts, including the Kentucky Derby as the 3-2 favorite.

If you played the favorite angle going into the Super Bowl, you likely cashed a winning ticket. The Dolphins (-1 point) defeated the Redskins by the score of 14–7, and became the first and still the only team in NFL history to complete a perfect, undefeated season culminating with a championship. 

1973/1974 — Secretariat — Miami Dolphins

Favorites were the play: Secretariat went off as the 3-2 favorite (as part of an entry with stablemate Angle Light) and raced to what still stands today as a scintillating track record of 1:59​²⁄₅ in the Derby. 

The Dolphins, 6 ½-point favorites appearing in their third consecutive Super Bowl, defeated the Vikings by the score of 24-7 to win their second straight Super Bowl.

1974/1975 — Cannonade — Pittsburgh Steelers      

Another year, another set of favorites: Cannonade went to the post along with 22 other horses in the largest Derby field ever as part of the favored entry along with stablemate Judger.

The Steelers, a three-point favorite, defeated the Minnesota Vikings 16-6 in a defensive struggle, capturing their first of six Super Bowl titles.

1975/1976 — Foolish Pleasure — Pittsburgh Steelers     

Foolish Pleasure was an undefeated champion as a 2-year-old and captured the Kentucky Derby as the favorite. 

Super Bowl X featured a contrast of playing styles between the Steelers, favored by 6 ½ to 7 points, and the Dallas Cowboys, which were at the time arguably the two most popular teams in the league. 

Once again, the favorite ultimately prevailed as the Steelers repeated as Super Bowl champion with a 21-17 victory, but they failed to cover the spread.

1976/1977 — Bold Forbes — Oakland Raiders

In the 1976 Kentucky Derby, Bold Forbes (who paid $8 on a $2 bet) led from the start, setting a “blistering pace,” and won by a length from 2-5 favorite Honest Pleasure.

The bold, mean, nasty, and favored Oakland Raiders easily covered the four-point spread, defeating the Minnesota Vikings 32-14 to capture their first Super Bowl victory.

1977/1978 — Seattle Slew — Dallas Cowboys

Seattle Slew, the heavy favorite at odds of 1-2, captured the 1977 Kentucky Derby. As Joe Hirsch of the Daily Racing Form wrote: “‘Slewmania’ was a virulent and widespread condition.” And, well before social media.

Seeing a pattern here? Again, the favorite covered relatively easily as the Dallas Cowboys, six-point favorites, easily defeated the Denver Broncos 27-10.

1978/1979 — Affirmed — Pittsburgh Steelers

Alydar entered the Kentucky Derby as a slight favorite over his familiar rival Affirmed, but it was Affirmed who prevailed, paying $5.60 on a $2 bet as the 9-5 second betting choice.

This was the first Super Bowl that featured a rematch of a previous one (the Steelers had previously beaten the Cowboys, 21–17, in Super Bowl X), and both teams were attempting to be the first club to ever win a third Super Bowl.

The point spread for the game opened at Pittsburgh -3 1/2 points before eventually settling at Pittsburgh at -4 by game time. The Steelers’ 35-31 victory meant the Las Vegas sportsbooks lost the vast majority of wagers on the game. The game thus came to be known as “Black Sunday” in Las Vegas.

1979/1980 — Spectacular Bid — Pittsburgh Steelers       

Spectacular Bid, the 3-5 betting favorite, raced to a 2 ¾-length victory.

Similar to Spectacular Bid, the Pittsburgh Steelers were heavily favored (-10 to 10 ½ points) to win Super Bowl XIV and become the first team to win four Super Bowls. The Steelers scored 14 unanswered points in the fourth quarter to defeat the Los Angeles Rams 31-19 and covered the spread.

1980/1981 — Genuine Risk — Oakland Raiders

In a stunner, Genuine Risk won the 1980 Kentucky Derby (paying $28.60 on a $2 bet), becoming, at the time, only the second filly to ever capture the run for the roses.

Following that form, the Oakland Raiders became the first underdog (+3 points) to win the Super Bowl outright since Baltimore in Super Bowl V, defeating the favored Philadelphia Eagles 27-10.

1981/1982 — Pleasant Colony — San Francisco 49ers

Pleasant Colony (who paid $9 on a $2 bet) held off a powerful stretch drive by Woodchopper to win the 1981 Kentucky Derby by three-quarters of a length.

Super Bowl XVI opened as a pick-’em between the Cincinnati Bengals and San Francisco 49ers. The line soon moved to San Francisco -2 before the Bengals actually closed as one-point favorites. However, it was the 49ers who prevailed 26-21.

1982/1983 — Gato del Sol — Washington Redskins

Gato del Sol was winless going into the 1982 Kentucky Derby and thus was sent off at odds of 21-1, the third longest in the race. He paid $44.40 to win, the 12th highest payoff in Derby history.

Super Bowl XVII came at the end of a season that was significantly shortened by a players’ strike. This was the third time the Dolphins were the favorites in the Super Bowl, but unlike Super Bowls VII and VIII, they did not win or cover. Instead, the underdog Redskins (+3 points) prevailed 27-17. Miami, which led by 7 at halftime, was outscored by the Redskins 17-0 in the second half as John Riggins rushed for 166 yards. 

1983/1984 — Sunny’s Halo — Los Angeles Raiders

Coming off a victory in the Arkansas Derby, Sunny’s Halo, with jockey Eddie Delahoussaye aboard, captured the 1983 Kentucky Derby against a very strong field and paid $7 on a $2 bet.

The underdog Los Angeles Raiders (+3 1/2 points) dominated the Washington Redskins in Super Bowl XVIII, winning 38-9 behind Marcus Allen’s 191 rushing yards.

1984/1985 — Swale — San Francisco 49ers

After an up-and-down start to his 3-year-old campaign, Swale won the 1984 Derby, paying $8.80 on a $2 bet.

Super Bowl XIX was hyped as the battle between two great quarterbacks — a match race, if you will, between Miami Dolphins QB Dan Marino and San Francisco’s Joe Montana. The 49ers were made three-point favorites and cruised to a 38-16 victory. This also marked the first Super Bowl to feature an over/under in the 50s.

1985/1986 — Spend a Buck — Chicago Bears

Spend a Buck won the 1985 Kentucky Derby under jockey Angel Cordero Jr. by 5 3/4 lengths over Stephan’s Odyssey, paying $10.20 on a $2 bet.

The Chicago Bears, the first double-digit favorite in the Super Bowl since the Pittsburgh Steelers in Super Bowl XIV, left no doubt as to their double-digit (10 points) favorite status, rolling over the New England Patriots 46-10.

1986/1987 — Ferdinand — New York Giants

From the very undesirable post position number one, Ferdinand, with Hall of Fame jockey Bill Shoemaker aboard, captured the 1986 Derby and paid $37.40 on a $2 bet.

The underdog Denver Broncos (+9 1/2) gave the New York Giants a first-half scare, before the Giants outscored Denver 30-10 in the second half to pull away for a 39-20 victory and cover the spread.

1987/1988 — Alysheba — Washington Redskins

Despite nearly falling to the ground at the top of the stretch when clipping heels with Bet Twice, Alysheba recovered and won the 1987 Derby, paying $18.80 on a $2 bet.

Denver arrived to Super Bowl XXII as the favorite (-3 1/2), and quickly got out to a 10–0 lead at the end of the first quarter of Super Bowl XXII. However, the underdog Redskins scored 42 unanswered points, including a record-breaking 35 points in the second quarter, to rout the Broncos 42-10.

1988/1989 — Winning Colors — San Francisco 49ers

Winning Colors is one of only three fillies to ever win the Kentucky Derby, paying $8.80 on a $2 bet. She went up against a stellar field of colts in the 1988 Kentucky Derby that included Risen Star, Seeking the Gold, Forty Niner, and co-favorite Private Terms. 

While San Francisco closed as a seven-point favorite, it took an 11-play drive culminating with the game-winning touchdown pass from Joe Montana to John Taylor with 34 seconds left to vault the 49ers to a 20-16 victory. But if you took the Cincinnati Bengals and the points, you scored that Super Bowl Sunday.

1989/1990 — Sunday Silence — San Francisco 49ers

As the 1989 Kentucky Derby approached, a budding rivalry developed between the East Coast-based Easy Goer and the West Coast-based Sunday Silence. In what was their first meeting, Sunday Silence, with jockey Pat Valenzuela aboard, defeated Easy Goer by 2½ lengths on a muddy track in the slowest time (2:05) for a Kentucky Derby since 1958, paying $8.20 on a $2 bet.

On Sunday, Jan. 28, 1990, the San Francisco 49ers, 12-point favorites, silenced the Denver Broncos in a 55-10 rout.

1990/1991 — Unbridled — New York Giants

Unbridled, with jockey Craig Perret aboard, won America’s most prestigious race by 3½ lengths over second betting choice Summer Squall. Unbridled paid $23.60 on a $2 bet.

Super Bowl XXV witnessed the underdog New York Giants (+6 1/2 points) winning outright, 20-19, as the Buffalo Bills’ Scott Norwood missed a potential game-winning 47-yard field goal in the closing seconds to break the hearts of Bills’ fans and send Giants fans into hysteria.

1991/1992 — Strike the Gold — Washington Redskins

Strike the Gold did just that in the 1991 Kentucky Derby, outrunning the betting favorite Hansel (who finished 10^th) and the bettor’s second choice, Fly So Free (who finished fifth). Strike the Gold paid $11.60 on a $2 bet.

The seven-point favorite Washington Redskins jumped out to a 17-0 lead at halftime and went on to cover the spread with a convincing 37-24 victory over the Buffalo Bills.

1992/1993 — Lil E. Tee — Dallas Cowboys

According to his assistant trainer, the racehorse was named Lil E. Tee "because he was so ugly and gangly when he was a foal that he reminded them of E.T., the extraterrestrial creature in the Steven Spielberg movie.” 

Lil E. Tee started in post position 10 and was ridden by jockey Pat Day, who hadn’t won a Derby in nine previous attempts. Post 10 was, indeed, the lucky charm as Lil E. Tee captured the 1992 Derby and paid $35.60 on a $2 bet.

Despite making their third straight Super Bowl appearance, the Buffalo Bills, +6 1/2 underdogs, were no match for the Dallas Cowboys. The Cowboys scored 35 points off of a Super Bowl-record nine Buffalo turnovers to run away with a 52-17 victory.

1993/1994 — Sea Hero — Dallas Cowboys

Sea Hero, who was winless in his first three starts as a 3-year-old, entered the 1993 Derby as a 12.90-1 longshot and pulled off the upset by ​2 ¹⁄₂ lengths over Prairie Bayou, the lukewarm betting favorite. 

In a repeat Super Bowl of the year before, the Buffalo Bills closed as 10 1/2-point underdogs, the largest point spread of their four Super Bowl appearances, and were yet again soundly defeated by the Dallas Cowboys 30-13. After trailing 13–6 at halftime, the Cowboys scored 24 unanswered points in the second half. 

1994/1995 — Go for Gin — San Francisco 49ers

Go for Gin entered the 1994 Kentucky Derby at 9.10-1 odds, behind Holy Bull at 2.20, Brocco at 4.30, Tabasco Cat at 6.10, and Strodes Creek at 7.90. On a sloppy track, Go for Gin won by two lengths in a time of 2:03.72.

Super Bowl XXIX saw the biggest opening-line favorite in Super Bowl history (-17 1/2). The San Francisco 49ers (who closed as 19-point favorites) cruised to an easy 49-26 victory over the San Diego Chargers to cover the spread. The combined aggregate score of 75 points and the 10 total touchdowns both remain Super Bowl records.

1995/1996 — Thunder Gulch — Dallas Cowboys

Thunder Gulch, who was one of three horses entered in the 1995 Derby by trainer D. Wayne Lukas, was sent off in the race at 24.50-1 odds with jockey Gary Stevens aboard. From post position 16, Thunder Gulch captured the 121^st Derby in a time of 2:01.27.

In a match-up of the Pittsburgh Steelers versus the Dallas Cowboys, the heavily favored Cowboys (-13 1/2) won their third Super Bowl in four seasons 27-17, but failed to cover the spread. Another payday for the underdog play.

1996/1997 — Grindstone — Green Bay Packers

Grindstone edged Cavonnier at the finish line to win the 1996 Kentucky Derby and paid $13.80 on a $2 bet. Jockey Jerry Bailey earned his second Derby victory and trainer D. Wayne Lukas was a back-to-back winner. Five days after his Derby victory, Grindstone was retired when a bone chip was discovered in his knee.

Super Bowl XXXI between the Green Bay Packers (14-point favorites) and the New England Patriots ended in a push as the Packers claimed the championship 35-21.

1997/1998 — Silver Charm — Denver Broncos

Silver Charm was ridden by Gary Stevens and trained by Bob Baffert. He went off at 4-1 odds, breaking from post position five among a field of 13 entrants and finished a head in front of Captain Bodgit. Silver Charm missed the Triple Crown by three-quarters of a length to Touch Gold in the Belmont Stakes. He now calls Old Friends Farm home and is the oldest living winner of the Preakness Stakes.

After suffering four previous Super Bowl losses, the Denver Broncos became the first double-digit underdog to win the Super Bowl since the Kansas City Chiefs in Super Bowl IV, defeating the Packers 31-24. The line opened with the Broncos as a 14-point underdog, but eventually moved to 11 ½ points at kickoff.

1998/1999 — Real Quiet — Denver Broncos

Nicknamed "The Fish" by his trainer due to his narrow frame, the lightly regarded Real Quiet captured the 1998 Kentucky Derby with jockey Kent Desormeaux aboard and paid $18.80 on a $2 wager. He came up just a nose short of winning the Triple Crown when nipped by Victory Gallop in the Belmont Stakes.

A double-digit underdog the previous year, the Denver Broncos entered Super Bowl XXXIII against the Atlanta Falcons as a 7 1/2-point favorite. Denver scored 17 consecutive points to jump to a 17–3 lead in the second quarter and went on to an easy 34-19 victory.

1999/2000 — Charismatic — St. Louis Rams

Pitted against 18 other horses, Charismatic, a 31.30-1 longshot in the 125^th run for the roses, withstood a late charge from Menifee to win by a head and deny trainer Bob Baffert his third consecutive Derby win while sending ecstatic winning bettors to the windows to cash in on the longshot payday.

While the first 30 Super Bowls produced no Against the Spread (ATS) pushes, this game between the St. Louis Rams (seven-point favorites) and Tennessee Titans produced the third push of a point spread or over/under total in four years. This game, which became known as the "Dot-com Super Bowl" due to the large amount of television ads purchased by dot-com companies, came down to the final play. Rams linebacker Mike Jones tackled Tennessee wide receiver Kevin Dyson one yard short of the goal line, dashing the hopes and dreams of the Titans and sending St. Louis to its first Super Bowl victory.

2000/2001 — Fusaichi Pegasus — Baltimore Ravens

Fusaichi Pegasus raced to victory in the 2000 Kentucky Derby and became the first favorite to win the Derby since Spectacular Bid in 1979. 

The Baltimore Ravens, who closed as three-point favorites and were led by their stifling defense, shut down the New York Giants 34-7, holding them to 152 yards of offense (the third-lowest total ever in a Super Bowl), en route to becoming the third wild card team to win the Super Bowl and the second in four years.

2001/2002 — Monarchos — New England Patriots

Despite being the sixth betting choice for the 2001 Kentucky Derby, Monarchos, a gray or roan colt, pulled away in the final furlong to win by nearly 4 3/4 lengths, paying $23 on a $2 bet. His winning time of 1:59.97 for 1¼ miles proved to be in the second-fastest winning time in the race’s history.

The underdog theme carried over to the Super Bowl. Entering Super Bowl XXXVI, the New England Patriots were 14-point underdogs to the St. Louis Rams, who were making their second appearance in the last three years behind a high-powered offense dubbed “the greatest show on turf.” Although the Rams outgained the Patriots 427–267 by total yards, the Patriots capitalized on three key turnovers by the Rams to win 20-17 and become the second-biggest underdog ever to win a Super Bowl, behind only the Jets in Super Bowl III.

2002/2003 — War Emblem — Tampa Bay Buccaneers

Nicknamed “Hannibal Lecter” by trainer Bob Baffert for his habit of biting, Illinois Derby winner War Emblem was listed at 20.50-1 odds for the 2002 Kentucky Derby. While his jockey, Victor Espinoza, had never laid eyes on the horse until the morning of the race, it didn’t seem to matter. War Emblem took the early lead and eventually kicked away to the upset victory, paying $43 for a $2 win bet.

That form held true for Super Bowl XXXVII as the upstart Tampa Bay Buccaneers, four-point underdogs, fell behind the Oakland Raiders 3-0 before scoring 34 consecutive points to pound out a convincing 48-21 victory and a payday for those who backed the underdog.

2003/2004 — Funny Cide — New England Patriots

The run on underdogs at the Derby continued as Funny Cide — sent off as the bettors' eighth choice at 12.80-1 odds (the favorite was Empire Maker at 5-2) — became the first gelding since Clyde Van Dusen in 1929 and the first (and only, to date) New York-bred to win the Kentucky Derby.

In the last Super Bowl to feature an over/under in the 30s, the seven-point favorite New England Patriots and Carolina Panthers clashed in what many NFL scribes call one of the greatest Super Bowls of all time. Oddly enough, neither team scored in the first or third quarters and the game wasn’t decided until Adam Vinatieri kicked the winning field goal with seven seconds remaining to lift the Patriots to a 32-29 win. Yet, if you took the Panthers and the points, you won handsomely. And if you watched the halftime show, you were treated to the infamous “wardrobe malfunction” between Janet Jackson and Justin Timberlake.

2004/2005 — Smarty Jones — New England Patriots

The popular Pennsylvania-bred Smarty Jones became the first unbeaten Kentucky Derby winner since Seattle Slew in 1977 (he paid $10.20 on a $2 wager). Trainer John Servis and Canadian-born jockey Stewart Elliott became the first trainer-jockey combination in 25 years to win the Kentucky Derby in their debut appearance.

For the second straight season, the Patriots entered the Super Bowl as seven-point favorites, yet failed to cover the spread. Despite not covering, the Patriots became the second team after the Dallas Cowboys to win three Super Bowls in four years with their 24-21 victory over the Philadelphia Eagles.

2005/2006 — Giacomo — Pittsburgh Steelers

Giacomo, whose owner-breeder Jerry Moss was better known for co-founding A&M Records with trumpeter Herb Alpert, was named after the son of famous musician Sting.

Ridden by jockey Mike Smith, Giacomo stunned the world by winning the 2005 Kentucky Derby at odds of 50.30-1. He ranks as the fourth biggest longshot ever to win the Derby, trailing only Donerail, who went off at 91.45-1 in 1913; Country House at 65.20-1 in 2019; and Mine That Bird at 50.60-1 odds in 2009. The $2 exacta paid a whopping $9,814.80, the biggest exacta payoff in Derby history, as the 71.60-1 bomb Closing Argument finished a half-length behind Giacomo.

Despite being a four-point favorite, the Pittsburgh Steelers entered the Super Bowl with a monkey on Head Coach Bill Cowher’s back. While Cowher had shaped the Steelers into one of the top teams in the NFL — they made the playoffs in 10 out of his 14 seasons, reached the AFC Championship game six times, and had lost his only Super Bowl appearance to the Dallas Cowboys in Super Bowl XXX — he desperately craved the big win and Super Bowl ring. The second appearance proved to be the charm as the Steelers defeated the Seahawks 21-10 to improve to 5-1 ATS in the Super Bowl.

2006/2007 — Barbaro — Indianapolis Colts

Entering the 2006 Kentucky Derby among a full field of 20 horses, Barbaro was undefeated with a perfect 5-for-5 record and was the second choice of the betting public, at odds of 6.10-1. Barbaro cruised to a 6 ½-length victory, the largest margin at the Derby since 1946, when Triple Crown winner Assault won the run for the roses by eight lengths. Barbaro’s win also established him as only the sixth undefeated horse to prevail in the Kentucky Derby.

Super Bowl XLI featured two teams ending long Super Bowl appearance droughts: The Colts who had not appeared since 1971 vs. the Bears who hadn’t been back since 1986. Under rainy, South Florida conditions, the Colts, favored by a touchdown, overcame an eight-point first quarter deficit, and forced five turnovers en route to a 29-17 victory. While the game itself was watched by an estimated audience of 93.2 million, it was the halftime show by Prince that proved most captivating, peaking at 140 million television viewers.

2007/2008 — Street Sense — New York Giants

Rallying from a second-to-last, Street Sense beat Hard Spun by 2 ½ lengths to win the 2007 Derby, paying $11.80 to win on a $2 wager. Street Sense also became the first Breeders’ Cup Juvenile winner to add a Kentucky Derby victory and the first champion 2-year-old male to win the Derby since 1979, when Spectacular Bid achieved the feat.

Looking to become the first 19-0 team in NFL history, the New England Patriots were 12 ½-point favorites over the New York Giants heading into Super Bowl XLII. Considered one of the biggest upsets in the history of professional sports, the tight-and-tense game came down to the memorable Giants’ fourth quarter game-winning drive, which included the “Helmet Catch” by wide receiver David Tyree after quarterback Eli Manning eluded a sack. In the first Super Bowl since 1975 in which neither team scored more than 20 points, the Giants shocked the world with a 17-14 upset and pleased the 1972-1973 Miami Dolphins, as they remain the only team to complete an undefeated NFL season.

2008/2009 — Big Brown — Pittsburgh Steelers

Named in honor of the United Parcel Service (UPS), Big Brown captured the 2008 Kentucky Derby as the 2.40-1 favorite, becoming the first horse to win the Derby from post position 20 since Clyde Van Dusen in 1929.

The Big Brown to Big Ben connection didn’t pan out for the bettors however. The seven-point favorite Pittsburgh Steelers had to rally under quarterback Ben Roethlisberger to score with 35 seconds remaining to defeat the Arizona Cardinals 27-23, but failed to cover the spread.       

2009/2010 — Mine That Bird — New Orleans Saints

Mine That Bird entered the 2009 Kentucky Derby with the third-longest odds in the 19-horse field, with only Atomic Rain (55.20-1) and Join in the Dance (51.40-1) starting higher. Yet, despite a poor start, Mine That Bird, under the direction of Calvin Borel, used a ground-saving, rail-riding path that resulted in one of the biggest Derby shockers ever. He ended up winning by 6​³⁄₄ lengths for the longest margin of victory in more than 60 years. A $2 win wager on Mine That Bird returned $103.20, and five years later, in 2014, the story of Mine That Bird was turned into the movie “50 to 1,” directed by Academy Award winner and Thoroughbred owner and fan Jim Wilson.

Prior to the start of the 2009 season, the New Orleans Saints were 25-1 odds to win the Super Bowl. Not quite Mine That Bird odds, but still a pretty nice payday for those bold risk-takers with vision. The Saints, making their first Super Bowl appearance as 4 ½-point underdogs to the Peyton Manning-led Colts, used a surprised onside kick to start the second half and take their first lead in the game. In the end, the Saints culminated the upset with Tracy Porter’s 74-yard pick six against Peyton Manning resulting in a final score of 31-17.

2010/2011 — Super Saver — Green Bay Packers

On a wet and sloppy track, Super Saver captured the 2010 Kentucky Derby returning $18 on a $2 wager, as jockey Calvin Borel captured his third Derby in a four-year span. The win also provided trainer Todd Pletcher with his coveted first Kentucky Derby victory after years of numerous entries falling short.    

In their first four Super Bowl appearances, the Green Bay Packers were double-digit favorites, but against the Steelers in Super Bowl XLV, the Packers were only 2 1/2-point favorites. It didn’t matter as the outcome was never really in doubt as the Packers, who led the entire game, defeated the Steelers 31-25 to cover the spread.

2011/2012 — Animal Kingdom — New York Giants

In his first race on dirt, Animal Kingdom, trained by Graham Motion, drew post position 16 and was listed at 20.90-1 odds in the 2011 Kentucky Derby. Jockey John Velazquez originally was scheduled to ride the Derby favorite, Uncle Mo, but that horse was scratched due to a gastrointestinal illness on the Friday before the race and Velazquez picked up the mount aboard Animal Kingdom. From lemons to lemonade for Velazquez as his first time aboard Animal Kingdom proved fruitful: He won the race by 2 ¾ lengths, capturing his first Derby win in 13 attempts.

Considered by many to be a rematch of Super Bowl XLII, though this time the Patriots were only favored by three, the underdog New York Giants scored the game-winning touchdown with 1:06 left to defeat the Patriots 21-17. The Giants set a new record for the worst regular season record (9–7, win percentage of 56.3%) by a Super Bowl champion in earning their fourth Lombardi Trophy.

2012/2013 — I’ll Have Another — Baltimore Ravens

I’ll Have Another, 15.30-1 odds, became the first horse in the history of the Kentucky Derby to win from post position 19 as jockey Mario Gutierrez made his Derby debut a memorable one. Owner Paul Reddam claimed the horse’s named was inspired by his reply to when his wife inquired whether he wanted more of her homemade cookies.

Super Bowl XLVII pitted two brothers coaching against each other —Jim and John Harbaugh, head coaches of the four-point favorite San Francisco 49ers and Baltimore Ravens, respectively — for the first time ever. Despite a power outage in the Super Dome which caused a 34 minute delay in the game, the underdog Baltimore Ravens ran out to 28-6 lead and hung on for a 34-31 victory.

2013/2014 — Orb — Seattle Seahawks

Orb, trained by Kentuckian and Hall of Fame trainer Shug McGaughey, was sent off as the tepid favorite in the 139^th running of the Kentucky Derby. On a sloppy track, Orb pulled away to provide McGaughey with his first ever Derby win, leading him to exclaim post-race: “I’ve always dreamed of this day and it finally came.” On a $2 bet, Orb returned $12.80.

Super Bowl XLVIII represented only the third time the number one seed from each conference met in the Super Bowl. The Denver Broncos, behind five-time MVP Peyton Manning at quarterback, were the 2 ½-point favorites at game time, despite the initial line opening with Seattle -1 1/2.  However, the Seahawks scored the first 36 points of the game in a blowout 43-8 victory for the underdog.

2014/2015 — California Chrome — New England Patriots

California Chrome was made the 5-2 morning line favorite of the 2014 Kentucky Derby, despite the fact that prior to 2014, only three California-bred horses had won the Kentucky Derby: Morvich in 1922, Swaps in 1955, and Decidedly in 1962. From post position five, Chrome easily ran the best race, led by five lengths in early stretch, and coasted past the finish line as the victor while “Chromies” rejoiced.

For the second consecutive year, the Pete Carroll-coached Seahawks opened as a favorite in the Super Bowl (this time -3) before closing as a one-point underdog to the New England Patriots. With 26 seconds remaining in the game and the Patriots ahead 28-24, Seattle unexpectedly decided to pass the ball in what became a highly scrutinized and questioned play call. The result was Patriots undrafted rookie Malcolm Butler jumping the route to intercept the pass and preserve the Patriots' four-point victory as more than 120 million viewers watched the drama-filled ending.

2015/2016 — American Pharoah — Denver Broncos

American Pharoah emerged as the betting favorite (2.90-1 odds) among a competitive field of 18 racehorses in the 141^st running of the Kentucky Derby. In what proved to be his most challenging race on the way to eventually completing the first Triple Crown sweep since Affirmed in 1978, American Pharoah took the lead entering the final furlong and won by a length ahead of Firing Line. Jockey Victor Espinoza, who won the race for the third time, exalted post-race: “I feel like the luckiest Mexican on earth.”

The Golden Anniversary of the NFL’s Super Bowl featured the Carolina Panthers as five-point favorites against the Denver Broncos. Denver, which entered the game 1-3 ATS as an underdog in the Super Bowl, relied on a dominant defense to foil Panthers quarterback Cam Newton and lead the Broncos to the convincing 24-10 win.

2016/2017 — Nyquist — New England Patriots

Named after Detroit Red Wings star Gustav Nyquist by owner Paul Reddam, Nyquist, the 2.30-1 favorite for the 2016 Derby, broke from post position 13 and pressed the pace before drawing away from the field in the stretch, holding off Exaggerator by 1 ¼ lengths for the win.

Overcoming a 28-3 deficit late in the third quarter to the Atlanta Falcons, Tom Brady led the favored (-3) New England Patriots to the greatest Super Bowl comeback ever. The Patriots scored the final 25 points in regulation to force the first overtime Super Bowl game. The Patriots won the coin toss, marched down the field and scored the game-winning touchdown, and covered the spread with the 34-28 OT victory for the ages.

2017/2018 — Always Dreaming — Philadelphia Eagles

Coming off an impressive Florida Derby win, Always Dreaming was made the 4.70-1 Derby favorite on a wet-fast racetrack. Always Dreaming pulled away in the stretch to become trainer Todd Pletcher's second Derby winner.

The New England Patriots, making their record 10th appearance in a Super Bowl and third in the last four years, were favored by four points over the Philadelphia Eagles. However, the Eagles pulled out the “Philly Special” to defeat the Patriots in a 41-33 shootout, becoming the third team in the Super Bowl era to win every postseason game as an underdog, joining the 2007 New York Giants and 1980 Oakland Raiders.

2018/2019 — Justify — New England Patriots

Despite not making his first start until Feb. 18, 2018, Justify entered the 2018 Kentucky Derby as the 2.90-1 favorite. He cemented his legacy by winning the Derby by 2 ½ lengths over Good Magic. Justify also ended what was known as the “Curse of Apollo.” No horse had won the Kentucky Derby without competing in a race as a 2-year-old since Apollo in 1882. Justify went on to become the 13th horse to sweep the Triple Crown.

The matchup of the New England Patriots, favored by two points, and the Los Angeles Rams in Super Bowl LIII proved to be the lowest-scoring Super Bowl game in history. New England scored 10 points in the fourth quarter to break the 3-3 defensive struggle and earn its sixth Super Bowl title.

2019/2020 — Country House — Kansas City Chiefs

The 145^th running of the Kentucky Derby proved to be one of the more controversial, confusing, and tense endings ever. While Maximum Security crossed the finish line first on the sloppy racetrack, a 22-minute delay ensued as the jockeys of Country House and Long Range Toddy each filed an objection to the result. After an extended review, the stewards decided that Maximum Security had indeed compromised War of Will and Long Range Toddy when he swerved into their path. As a result, the second-place finisher, Country House at 65.20-1 odds, was elevated to first place and crowned 2019 Kentucky Derby champion. Maximum Security, meanwhile, was disqualified and placed 17^th. 

The payout on a $2 bet on Country House was $132.40 and the $1 superfecta paid $51,400.10.

In the following Super Bowl, it also appeared there would be a different winner than what turned out to be the eventual champion.  The San Francisco 49ers controlled most of the game and still had a 20-10 lead as the game was halfway through the fourth quarter. Just as it looked like the 49ers were on their way to becoming the next Super Bowl winner, it was not to be. Kansas City Chiefs quarterback Patrick Mahomes took control in the late stages of the game and led the Chiefs to a 21-point fourth quarter rally to defeat San Francisco 31-20.

2020/2021 — Authentic — Tampa Bay Buccaneers

The Covid-19 pandemic affected just about everything in society for much of 2020, and sports and horseracing were no exception. For horseracing, the most monumental shift occured with the changing of the date of the Kentucky Derby away from its traditional slot on the first Saturday in May. The race ended up being run instead on the first Saturday in September. It doesn't have the same ring, does it? In addition to being run four months late, the Kentucky Derby was also run out of order in the 2020 Triple Crown. For the first time in history, the Belmont Stakes was run as the first race of the 2020 Triple Crown. Belmont Stakes winner Tiz the Law was upset in the Kentucky Derby by the winner, Authentic.

The more things changed in the 2021 Super Bowl, the more they stayed the same. It was an all new team taking the title with the Tampa Bay Buccaneers beating the defending champion Kansas City Chiefs, 31-9, but the man at the helm of the Super Bowl champions was a familiar one -- it was Tom Brady.  In many ways, as strange as it was to see the previous Kentucky Derby being run in September instead of May, it was even stranger to see Tom Brady in the Tampa Bay uniform instead of the New England Patriots uniform he had worn for his nine previous Super Bowl appearances and his six previous Super Bowl victories. In the end, it was the quarterback that mattered more than the uniform, and the result for Tom Brady was more of the same – another Super Bowl championship.

2021/2022 — Mandaloun — Los Angeles Rams

Medina Spirit was the original winner of the 2021 Kentucky Derby, but he was later disqualified when it was alleged an illegal substance was present in his post-race sample. The original runner-up, the much less accomplished and unheralded Mandaloun, was awarded first place.  Medina Spirit became the second Kentucky Derby disqualification in the span of three years.

Thankfully the following Super Bowl was much less controversial than the previous Kentucky Derby. The Los Angeles Rams, who were favored by 3.5 points after a 12-5 regular season record, came from behind to defeat the Cincinnati Bengals, 23-20. The game was played at the Rams' home field at SoFi Stadium in Englewood, Calif. (which sits on the former site of Hollywood Park). The game featured three lead changes, but none sparked the kind of controversy that affected the 2021 Kentucky Derby.

2022/2023 — Rich Strike — ???

The 2022 Kentucky Derby was won by the longest shot in the race, the 80.80-1 odds Rich Strike. Originally on the also-eligible list, The No. 21 horse Rich Strike drew into the Kentucky Derby the day before the race and almost went into the race completely un-noticed. He went on to pull-off one of the biggest upsets in the history of the Kentucky Derby thanks to a very fast pace that helped set-up his late closing rally along with the brilliant ride of a lifetime from journeyman jockey Sonny Leon.

That brings us to the 2023 Super Bowl. Before the start of the season, the Kansas City Chiefs were among the favorites to win the Super Bowl, while the Philadelphia Eagles were coming off a solid but not spectacular 9-8 record in 2021 and were listed at 24-1 to win the Super Bowl before the season. Twelve other teams were favored ahead of them. While not longshots to the degree that Rich Strike was in the Super Bowl, it is fair to say that the Philadelphia Eagles winning the Super Bowl would have to be considered an upset as compared to their pre-season outlook.

So, if you are playing along at home, there really is no Rich Strike of Super Bowl LVII. The Eagles and Chiefs finished the regular season with identical 14-3 records, and both teams were the No. 1 seed in the playoffs in their respective conferences. The point spread of the Super Bowl says has the Eagles favored by 1.5 points. If you are betting the Super Bowl to correspond with the Kentucky Derby, that means you are predicting an upset. It's not a big upset, but the underdogs this year are the Kansas City Chiefs.