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2020 Kentucky Oaks Betting Breakdown and Best Bets

Before Saturday's 146th "Run For The Roses," the fillies take center stage on Friday in The "Kentucky Oaks." SI Gambling insider Frankie Taddeo handicaps the celebrated race from Churchill Downs and offers his best bets!

Want to know who will win the Kentucky Derby? Our expert handicappers predict who will win and how to bet the exacta and trifecta exotics.

The SI Gambling Horse handicapping experts had a great day at the track in the Travers Stakes when Tiz the Law came through in impressive fashion, helping our team crush the Exacta (8/1) and the Trifecta (36/1) after Caracaro & Max Player both hit the board!

In July, the team scored in the Blue Grass Stakes hitting the Exacta (12/1), Trifecta (60/1) and Superfecta (443/1). Now, the boys are back with some sharp opinions for this Saturday.

This weekend, racing fans will be treated to arguably the biggest weekend of the horse racing calendar, when the Kentucky Oaks and the Kentucky Derby take center stage of the sports world.

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The $1,250,000 Kentucky Oaks draws an ultra competitive field of nine three-year-old fillies. Gamine (1/1) enters as the even-money favorite off two straight impressive wins in the Acorn Stakes (G1), at Belmont, and the Test (G1) at Saratoga. Bob Baffert’s star girl drew post No. 5 and is primed to take the Oaks with John Velazquez in the saddles.

Swiss Skydiver (8/5) enters as the second choice after drawing the rail. Ken McPeek’s top filly is in superb form winning four of her last five races. Her only blemish was when she attempted to take on the boys and came up just short behind Art Collector in the Blue Grass Stakes at Keeneland in July.

Rounding out the top contenders is Mike McCarthy’s Speech (5/1) who opened some eyes in her win in the Ashland Stakes (G1) at Keeneland back on July 11. In that race she won going away and defeated Venetian Harbor, Envoutante and Bonny South. She ran second to Swiss Skydiver in the Santa Anita Oaks back in June, and will now look to flip the tables with Javier Castellano aboard.

The other six fillies in the field are all listed at odds of 15-1 or higher. Simon Callaghan’s Donna Veloce (15/1), by Uncle Mo, who drew post No. 3 and Anthony Margotta’s Hopeful Growth (30/1) who drew post No. 8 should be looked at as longshots to possibly hit the board and round out trifecta and superfecta tickets.

Who will cross the finish line first? Let’s take a look at the odds and dive deeper into these races.

Kentucky Oaks (G1)

Racetrack: Churchill Downs, Louisville, Kentucky

Date: Friday, September 4, 2020

Purse: $1,250,000

Distance: 1 ⅛ mile, Dirt

Race: 12

Post Time: 5:43 p.m. EST / 2:43 p.m. PST


HORSES OF NOTE: Listed by post number, name, and odds

#5 Gamine (1/1) - There's simply no way to ignore Bob Baffert’s prized girl’s recent form. She has a win in the Test Stakes (G1) by seven lengths and in the Acorn by a whopping 18 lengths! If she gets loose on an uncontested lead she is taking this field of girls wire-to-wire. Top Choice

#1 Swiss Skydiver (8/5) - This filly must be respected but I think drawing the rail could be her biggest issue here. She will need to fire out of the gate and keep pace with Gamine, but will that hurt her chances at the extended distance demanded in the Oaks? Contender

#4 Speech (5/1) - She was impressive in her win last out in the Ashland Stakes but the formula is suggesting she is best used underneath. Exotic Play

Kentucky Oaks Formula Rankings

  • #5 Gamine (J: J. Velazquez; T: B. Baffert)
  • #1 Swiss Skydiver (J: T. Gaffalione; T: K. McPeek)
  • #4 Speech (J: J. Castellano; T: M. McCarthy)
  • #3 Donna Veloce (J: R. Santana; T: S. Callaghan)
  • #8 Hopeful Growth (J: TBD; T: A. Margotta)
  • #7 Shedaresthedevil (J: F. Geroux; T: B.Cox)
  • #6 Bayerness (J: R. Berejano; T: C. Devaux)
  • #2 Tempers Rising (J: J. Leparoux; T: D. Stewart)
  • #9 Dream Marie (J: J. Talamo; T: M. Williams)

Kentucky Oaks Betting Breakdown

Frankie Taddeo, SI Gambling & Fantasy Analyst / Vegas Insider (@Frankie_Fantasy)

This race will boil down to a combination of the top two entries. My top play is #5 Gamine (1/1) who I will use over #1 Swiss Skydiver (8/5) and #4 Speech (5/1). In trifecta and superfecta plays, I will be using longshots #3 Donna Veloce (15/1) and #8 Hopeful Growth (30/1) looking to spice up the payouts.

TOP Exacta: 5 -1             $1 wager: $1

Exacta P/W: 1,5/1,5,4      $1 wager: $4

TOP Trifecta P/W: 5 with 1 with 3,4,7,8   $1 wager: $4

Bomb Trifecta P/W: 5 with 3,4,7,8 with 1,3,4,7,8      ¢.50 wager: $8

SPREAD Trifecta P/W: 1,5 with 1,4,5 with 1,3,4,5,7,8   ¢.50 wager: $8

TOP SUPERFECTA: 5 with 1 with 3,4,8 with 3,4,7,8   $1 wager:$9

SUPERFECTA P/W: 1,5 with 1,5 with 3,4,8 with 3,4,7,8   ¢.50 wager: $9

All wagers display ticket cost. All bettors should adjust wager amounts based upon bankroll


Destin Heath, Trainer at Winstar Farms, Versailles, KY (@dgheat02)

Top Choice: #1 Swiss Skydiver (8/5)

Use Underneath: #5 Gamine (1/1) #4 Speech (5/1)

Favorite Longshots: #2 Tempers Rising (50/1) and #7 Shedaresthedevil (20/1)

“I really don’t like the angle of going sprint to route in big stakes races and that is why I am choosing to use Swiss Skydiver (despite drawing the rail) on top of Gamine and Speech,” said Heath.

Don't forget to check back for our best bets for the Kentucky Derby at SI Fantasy PRO!