Betting With Bobby: Flay Tackles Retired Soccer Player Michael Owen

Pop Culture

The road to the Breeders’ Cup is underway, and prep season is heating up. If there’s anyone who can take the heat, it’s celebrity chef and Breeders’ Cup ambassador Bobby Flay. Not only is Flay one of the best-known restaurateurs and TV personalities, he’s also heavily involved in the sport of racing as an owner and a fan. He can also handicap the races with the best of them!

In collaboration with Breeders’ Cup, America’s Best Racing is excited to present “Betting with Bobby,” a multi-week charity challenge series in which Flay is putting up his selections in key prep races against those of other Breeders’ Cup celebrity ambassadors.

In Round 1, Bobby defeated TV personality Carson Kressley in a Stephen Foster Stakes showdown. In Round 2, Bobby was bested by actress Jamie-Lynn Sigler in a Belmont Derby challenge. In Round 3, one of the greatest golfers of all time, Gary Player, defeated Bobby.

Actress Bo Derek and Bobby's picks made up the Whitney Stakes exacta in Round 4, but Bo came out on top with her pick of Whitney winner McKinzie. Bo's win meant $1,000 was donated to support #IAmHorseRacing while $500 was donated to the Thoroughbred Retirement Fund. In round 5, Bobby faced off against Colorado Avalanche star Erik Johnson. Neither Bobby or Erik picked Fourstardave winner Got Stormy so each star received $750 each for their respective charities.

This week, Bobby Flay and Michael Owen, a retired pro soccer player and racehorse owner, will face off with picks for the $1 million Pennsylvania Derby at Parx Racing. This week, Flay is playing for Permanently Disabled Jockeys Fund (PDJF) and Owen is playing for Alder Hey Children’s Charity. 

Let’s take a look at the rules and the 2019 “Betting with Bobby” race schedule:

How It Works:

Bobby Flay has challenged his fellow Breeders' Cup ambassadors in the ultimate betting challenge. Each Breeders' Cup Challenge Series telecast on NBC or NBCSN, Bobby will face off in a celebrity betting challenge by picking one main selection and one alternate for each race. Pride and a serious donation to charity will be on the line each week with the winner receiving $1,000 to donate to their charity of choice with the loser receiving a $500 donation.

Betting with Bobby


Each player has been asked to select one horse to win this week’s designated race. If one player selects the winner of the race and the other player doesn’t, the player with the correct selection is this week’s winner.

In the event that neither player correctly selects the winner of this week’s race, either player can still win if their horse finishes in the top three. Whichever player selects the horse who places higher in the top three will be this week’s winner.

If neither player correctly selects a horse who finishes in the top three, each player’s backup selection comes into play. If one player’s backup selection wins the race and the other player’s backup doesn’t, the player with the correct selection is this week’s winner.

In the event that neither player’s backup horse wins this week’s race, either player can still win if their horse finishes in the top three. If neither player’s backup horse finishes in the top three, this week’s matchup will be declared a tie.

Race Schedule:

Round 1: Stephen Foster Stakes, June 15. Bobby vs. Carson Kressley. Winner: Bobby Flay. 

Round 2: Belmont Derby Invitational, July 6. Bobby vs. Jamie-Lynn Sigler. Winner: Jamie-Lynn Sigler. 

Round 3: Haskell Invitational, July 20. Bobby vs. Gary Player. Winner: Gary Player.

Round 4: Whitney Stakes, Aug. 3. Bobby vs. Bo Derek. Winner: Bo Derek.

Round 5: Fourstardave Handicap, Aug. 10. Bobby vs. Erik Johnson. Winner: tie, both received $750 each for their respective charities.

Round 6: Pennsylvania Derby, Sep. 21. Bobby vs. Micheal Owen.

Round 7: Awesome Again Stakes, Sep. 28

Round 8: Claiborne Breeders’ Futurity, Oct. 5

Round 9: Juddmonte Spinster Stakes, Oct. 6


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