Using History to Handicap the 2020 Kentucky Oaks

Monomoy Girl (light blue jockey cap) battles for position during the 2018 Kentucky Oaks, a race she won by a half-length en route to championship honors at year’s end. (Eclipse Sportswire)

The Kentucky Derby Presented by Woodford Reserve isn’t the only historic race postponed due to COVID-19. Its companion event, the $1.25 million Grade 1 Longines Kentucky Oaks for 3-year-old fillies, has likewise been delayed from May 1 to Sept. 4.

A smaller field than usual is slated to contest the 1 1/8-mile race – as of Aug. 28, Churchill Downs lists 11 fillies as probably starters for the Kentucky Oaks. The emergence of two overwhelming favorites during the spring and summer has surely scared away a few fillies who might have taken part during the spring, so for the first time since 2014 a full field appears unlikely.

A smaller field isn’t the only impact of the Kentucky Oaks postponement. Prep race schedules have been turned upside down, leaving bettors to wonder how traditional handicapping rules and standards might apply to the reconfigured race.

The good news is, examining the recent history of the Kentucky Oaks reveals a number of trends that figure to remain relevant even with the postponement. To help guide you in the right direction, let’s use history to handicap the Kentucky Oaks, reviewing eight trends to keep in mind as the big race approaches.

Speed horses have an advantage

Positional speed is typically an important weapon in the Kentucky Oaks. Seven of the last 10 winners (and 11 of the last 15) were racing within 3 ½ lengths of the lead after the opening half-mile, which includes gate-to-wire winners Serengeti Empress (2019) and Summerly (2005).

This can be attributed in large part to the typically modest pace of the Kentucky Oaks. Unlike the Kentucky Derby, which often features quick fractions, the Kentucky Oaks tends to unfold in relaxed fashion. Over the last 15 years the fastest half-mile fraction has been :46.24, while the quickest time for three-quarters of a mile has been 1:11.25 – both modest splits by Grade 1 standards.

Occasionally, late runners do excel in the Kentucky Oaks; Abel Tasman (2017) closed from far behind to win over a sloppy track, while Princess of Sylmar (2013) and Blind Luck (2010) unleashed similarly big rallies over dry footing. But considering all three won a minimum of four Grade 1 races during their decorated careers, it’s safe to say it takes an elite filly to win the Kentucky Oaks in late-running style.



Position after first 1/2-mile

½-mile & ¾-mile times


Serengeti Empress

1st by 3 lengths (14 starters)

46.65, 1:11.26 (fast)


Monomoy Girl

2nd by 0.5 lengths (14 starters)

47.70, 1:11.49 (fast)


Abel Tasman

13th by 16.5 lengths (14 starters)

46.24, 1:11.42 (sloppy)


Cathryn Sophia

4th by 3 lengths (14 starters)

47.87, 1:12.60 (fast)


Lovely Maria

4th by 2 lengths (14 starters)

47.26, 1:11.50 (fast)



4th by 2 lengths (12 starters)

47.80, 1:12.24 (fast)


Princess of Sylmar

9th by 8 lengths (10 starters)

46.79, 1:11.34 (fast)


Believe You Can

2nd by 1 length (14 starters)

47.47, 1:11.88 (fast)


Plum Pretty

2nd by 3.5 lengths (13 starters)

46.99, 1:11.25 (fast)


Blind Luck

14th by 11 lengths (14 starters)

48.15, 1:12.50 (fast)

Respect fillies trained by Bob Baffert, Todd Pletcher, and Larry Jones

Since 1999, a trio of trainers have managed to win the Kentucky Oaks three times apiece. Hall of Fame conditioner Bob Baffert completed the hat trick with Silverbulletday (1999), Plum Pretty (2011), and Abel Tasman (2017). Todd Pletcher nabbed his three wins with Ashado (2004), Rags to Riches (2007), and Princess of Sylmar (2013). Larry Jones claimed victories courtesy of Proud Spell (2008), Believe You Can (2012), and Lovely Maria (2015).

In short, three trainers have accounted for 43% of Kentucky Oaks winners since 1999, so Baffert, Pletcher, and Jones all warrant respect whenever they send a filly to Churchill Downs.

Look for fillies who contested the Rachel Alexandra Stakes

In recent years, one race has exceeded all others as the most productive steppingstone toward the Kentucky Oaks. Since 2010, the 1 1/16-mile Grade 2 Rachel Alexandra Stakes at Fair Grounds has produced five Kentucky Oaks winners. Serengeti Empress (2019), Monomoy Girl (2018), and Untapable (2014) all managed to win both races, while Lovely Maria (2015) and Believe You Can (2012) parlayed defeats in the Rachel Alexandra into victories at Churchill Downs.

The Grade 2 Fair Grounds Oaks has also been an important prep race, producing half a dozen Kentucky Oaks winners since 2005. All told, 7 of the last 12 Kentucky Oaks winners ran at Fair Grounds during the winter of their 3-year-old seasons, establishing the New Orleans oval as a key proving ground for top Kentucky Oaks contenders.

A recent victory isn’t critical

While plenty of Kentucky Oaks winners have arrived at Churchill Downs off impressive victories, it’s almost as common for the eventual winner to suffer a defeat in her final prep race. Seven of the last 15 Kentucky Oaks winners (Serengeti Empress, Abel Tasman, Cathryn Sophia, Princess of Sylmar, Proud Spell, Lemons Forever, and Summerly) entered the race off a defeat, demonstrating that a last-out victory isn’t critical for success at Churchill Downs.

Longshots often outrun expectations

It’s common for unheralded fillies to step up with strong efforts in the Kentucky Oaks. Over the last 10 years, three fillies (Serengeti Empress, Princess of Sylmar, and Believe You Can) started at double-digit odds, while only two favorites (Untapable and Blind Luck) have managed to reach the winner’s circle.

In addition, 12 of the 30 Kentucky Oaks trifecta finishers (40%) started at double-digit odds, so looking for live longshots is critical if you want to cash high-paying exotic wagers.

Favor established stakes winners

Notwithstanding the above, unproven fillies rarely prevail in the Kentucky Oaks. You have to go back to Lemons Forever in 2006 to find a Kentucky Oaks winner who hadn’t previously won a stakes race. Even more impressively, 11 of the last 13 Kentucky Oaks winners had secured a graded stakes win prior to their success at Churchill Downs.

Upgrade fillies drawn in outside posts

Wide post positions have been anything but detrimental in the Kentucky Oaks. Since 2010, 12 of the 30 fillies to finish in the Kentucky Oaks trifecta (40%) started from post 10 or wider, a remarkable achievement considering these fillies represented just 24% of all Kentucky Oaks starters during the same timeframe.

Downgrade fillies breaking from posts 1 and 2

On the opposite end of the spectrum, fillies drawn in posts 1 and 2 have been disadvantaged in recent renewals of the Kentucky Oaks. The rail has not produced a single trifecta finisher in the last 15 years, while post 2 has produced only one top-three finisher during the same timeframe.

Bonny South (Coady Photography)


Pending the post position draw, history suggests the favorites will be formidable in the Kentucky Oaks. Four-time graded stakes winner Swiss Skydiver has an abundance of tactical speed and contested the Rachel Alexandra Stakes during the winter at Fair Grounds, while two-time Grade 1 winner Gamine is likewise a front-running force for trainer Bob Baffert. Assuming history holds true and the early pace isn’t destructive, Swiss Skydiver and Gamine will have every opportunity to run 1-2 all the way around Churchill Downs.

But the history of the Kentucky Oaks also hints we should respect the chances of graded stakes winners – preferably those entering off of defeats – who will be longshots in the wagering. Even if we don’t play them on top, they can be lucrative runners to use in the trifecta.

A perfect example is Bonny South, stretch-running winner of the Fair Grounds Oaks. The daughter of Munnings was bit dull when finishing fourth in the July 11 Grade 1 Central Bank Ashland Stakes in her first start off a four-month layoff, but she rebounded nicely in the Aug. 15 Grade 1 Alabama Stakes at Saratoga, closing ground strongly down the homestretch to finish second behind Swiss Skydiver.

Certainly Bonny South is a candidate to hit the board at a solid price. And if the battle between Swiss Skydiver and Gamine grows too intense, too soon, Bonny South might be capable of picking up the pieces at a big price.

Good luck with your handicapping, and enjoy the race!

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