It's time to head to Churchill Downs for the Kentucky Oaks — and time to place your horse racing bets on Friday's races — with the 2023 Kentucky Derby weekend is upon us.
Saturday will capture most of the horse-racing attention, but Friday is Kentucky Oaks Day with six stakes races leading up to the $1.25 million Kentucky Oaks, with the 2023 Kentucky Oaks post time set for 5:51 p.m. ET on May 5.
Below are our betting picks based on 2023 Kentucky Oaks odds, featuring predictions on all seven races.
2023 Kentucky Oaks Odds
| POST POSITION | HORSE | ODDS |
|---|---|---|
| 1 | Mimi Kakushi | 20-1 |
| 2 | The Alys Look | 15-1 |
| 3 | Gambling Girl | 15-1 |
| 4 | Southlawn | 8-1 |
| 5 | Wonder Wheel | 12-1 |
| 6 | Botanical | 4-1 |
| 7 | Wet Paint | 5-2 |
| 8 | Promiseher America | 30-2 |
| 9 | And Tell Me Nolies | 15-1 |
| 10 | Flying Connection | 15-1 |
| 11 | Defining Purpose | 12-2 |
| 12 | Dorth Vader | 20-1 |
| 13 | Affirmative Lady | 10-1 |
| 14 | Pretty Mischievous | 10-1 |
2023 Kentucky Oaks Picks
- Race 5: Win — No. 4 West Will Power
- Race 6: Win — No. 7 Shantisara
- Race 7: Win — No. 3 Olivia Twist
- Race 7: Pick 5 — 3,9 | 11 | 2,4,9,10 | 2,9,10 | 7
- Race 8: Pick 4 – 11 | 2,4 | 2,10 | 7
- Race 11: Win – No. 7 Wet Paint
*(Races 5-11)
Race 5 — Alysheba Stakes
Distance: 1 1/16 Miles
Surface: Dirt
Post Time: 12:43 p.m. ET, FS2
The Pick
No. 4 West Will Power (2-1) has been at his best since switching to the Brad Cox barn last summer. He’s run well at Churchill in the past and has been training smartly since his last start, where he produced his best Beyer speed figure. He looks primed and ready.
Live Contenders
No. 5 Smile Happy (8-1) only has one race in his career where he didn’t hit the board and that was last year’s Derby. That’s a race you can easily put a line through. He’s taken money or been the favorite in every start, except the Derby. While he will need to take a step forward to win, he’s worth a shot at these odds.
Race 6 — Modesty Stakes
Distance: 1 1/8 Miles
Surface: Turf
Post Time: 1:26 p.m. ET, USA Network
Top Pick
No. 7 Shantisara (2-1) won second off the layoff in her last time out. She’s won all three starts at this distance and figures to stalk the pace setter and get the first jump on any of the deep closers here. Trainer Chad Brown and jockey Flavien Prat have proven to be one of the best combos since Prat moved his tack east.
Race 7 — Eight Belles Stakes
Distance: 7 Furlongs
Surface: Dirt
Post Time: 2:09 p.m. ET, USA Network
Top Pick
No. 3 Olivia Twist (12-1) has had plenty of excuses from her past three starts. She lost to Wet Paint, the morning-line favorite. In addition, Olivia Twist clearly doesn’t like an off-track, so this pick is weather dependent. If the rain holds off and she gets a fast track, there’s enough speed here for her closing style. It’s also important to note that she’s cutting back distance, and based on her earlier career starts, she may be closer today, which would only improve her chances of an upset at a big price.
Live Contenders
No. 9 Munnys Gold (6-5) is a perfect 3-for-3 and has won by a combined 38 lengths. While that’s extremely impressive, she wasn’t facing much competition in any of those starts. Still, 38 lengths is 38 lengths. Her outside post position will allow her to choose her trip and if she’s as good as advertised, she will be tough here.
Race 8 — Unbridled Sidney Stakes
Distance: 5 1/2 Furlongs
Surface: Turf
Post Time: 3:03 p.m. ET
Top Pick
No. 11 Caravel (4-5) comes in off two consecutive wins over graded stakes company, both times against the boys. She is far and away the classiest horse in this field, and also the fastest. As long as she gets away cleanly, she should win.
Race 9 — La Troienne Stakes
Distance: 1 1/16 Miles
Surface: Dirt
Post Time: 4:04 p.m. ET, USA Network
Top Pick
No. 4 Secret Oath (3-1) was my Oaks pick last year and a horse I have always loved. She came back in her first start as a four-year-old with an impressive win over Clariere, who then turned the tables on her last time out. Secret Oath’s versatility and running style makes her a serious threat in this spot and we know she loves Churchill Downs.
Live Contenders
No. 2 Search Results (4-1) is an ultra-consistent mare, hitting the board in 10 of her 11 career starts. She’s lost to some of the absolute best fillies and mares in her division. Search Results owns the highest Beyer Speed figure in the field and while she’s coming in off a six-month layoff, she’s been training exceptionally well.
No. 10 A Mo Reay (5-1) is a perfect 3-for-3 since moving into the Brad Cox barn and continued to improve in each of those starts. If she’s able to continue that trend, she stands a big chance here. Her post position doesn’t help her though, as she will need to get over so as to not get caught too wide going into the first turn.
Race 10 — Edgewood Stakes
Distance: 1 1/16 Miles
Surface: Turf
Post Time: 4:51 p.m. ET, USA Network
Top Pick
No. 9 Papilio (7-2) won last time out at Keeneland, even while lugging in and looking extremely green in the stretch. If she had straightened up, she might have won by open lengths. She finished second to Danse Macabre, who came back to win her next two races. That makes Papilio’s second look even stronger. The biggest question for Papilio is will she have enough pace to run into.
Live Contenders
No. 10 Flashy Gem (10-1) has proven she can win from the front on the turf when she broke her maiden last summer. She came back as a three-year-old to win in front-running fashion on the synthetic and just wasn’t fast enough last time out, finishing second. However, she beat the third-place finisher by an impressive seven lengths. In a fairly paceless race, she has the ability to take this field gate to wire.
No. 2 Liguria (6-1) won as a favorite in her past two starts, albeit last year as a two-year-old. This is the first start off a six-month layoff and as a three-year-old, but if any trainer will have their horse ready on the turf, it’s Chad Brown.
Race 11 — Longines Kentucky Oaks
Distance: 1 1/8 Miles
Surface: Dirt
Post Time: 5:51 p.m. ET, USA Network
Top Pick
No. 7 Wet Paint (5-2) has been ultra-impressive in each of her three starts as a three-year-old. As a closer, she will need to work out a trip, but there’s enough pace in here for her to close into. She’s also proven she can do it regardless of track conditions, which is important to note as there is a possibility of rain.
2023 Kentucky Oaks Day Best Bets
Race 5: Win — No. 4 West Will Power
Race 6: Win — No. 7 Shantisara
Race 7: Win — No. 3 Olivia Twist
Race 7: Pick 5 — 3,9 | 11 | 2,4,9,10 | 2, 9,10 | 7
Race 8: Pick 4 – 11 | 2,4 | 2,10 | 7
Race 11: Win – No. 7 Wet Paint
