Kentucky Oaks Handicapping Picks
Horse racing gamblers are you looking for 2025 Kentucky Oaks Free Pick & Handicapping Odds…plus some predictions? Need some advice on who to take? The 2025 (G1) Kentucky Oaks is set for May 2 at Churchill Downs in Louisville, KY. Here’s a preview of our top contenders.
Kentucky Oaks Preview
- Race: Kentucky Oaks
- Purse: $1.5 million
- Distance: 1 1/8 miles
- Track: Churchill Downs
- Date: May 2, 2025
- Post Time: 5:51 PM (ET)
- Live: Kentucky Oaks Odds: Click Here
Before we can give you our expert 2025 Kentucky Oaks free pick, we have to break down the entries! In fact, we’d love to hear from you after you’ve given this post a read to see if you see an angle that we don’t!
2025 Kentucky Oaks Handicapping
In 2024, Thorpedo Anna won the Kentucky Oaks, and from there went on to have one of the best racing seasons we’ve seen in recent times. After the Oaks she had an undefeated season against her own gender, including scoring a win in the (G1) Breeders’ Cup Distaff.
Her only loss after the Oaks came by a narrow head when she went against males in the (G1) Travers Stakes, and that record was good enough to propel her to an Eclipse Award as Horse of the Year, the first three-year-old filly to do so since the great Rachel Alexandra in 2009.
All this is to say that while Friday’s Kentucky Oaks is often overshadowed by Saturday’s Kentucky Derby, the Oaks can feature high quality fields and superstar runners in its own right.
The Oaks is open to fillies age three, and they’ll run 1 1/8 miles on the Churchill Downs dirt course. The race has drawn a full field of 14 and includes one heavy favourite and lots of excellent betting value in the exactas and trifectas with 11 fillies in double-digits in the morning line odds.
Odds listed here are provided by the Churchill Downs track oddsmaker.
2025 Kentucky Oaks Free Pick & Handicapping: Good Cheer Race Odds: 6-5
Ever since breaking her maiden at first asking last August, Good Cheer has been literally unbeatable. Since that one-mile victory, she has won five straight, all at 1 1/16 miles and the last three of those in Grade 2 stakes.
Not only is she winning, she has essentially been toying with her rivals, with all her victories coming by open lengths, ranging from 2 1/2 to 17 lengths. Last out she sat her patented stalking trip, took over at the top of the stretch and went on to capture the (G2) Fair Grounds Oaks by 3 1/2 lengths.
2025 Kentucky Oaks Free Pick & Handicapping: Quietside Odds: 8-1
A winner of her last two consecutive races, Quietside has never been out of the money with three wins, three seconds and a third in her seven career starts. Last out she was a 3/4 length winner of the (G2) Fanatasy Stakes, going 1 1/16 miles at Oaklawn Park.
She’s one that likes to be up front pressing the pace, and in that regard she’s drawn a tough outside post and will have to be hustled early if she wants to get up and challenge the speed to her inside.
Simply Joking Race Odds: 10-1
Lightly raced Simply Joking will be making just her fourth career start after winning her first two and just coming up a 3/4 of a length short last out to Quiteside in the Fantasy.
A bump at the gate left her having to come from behind in her maiden win, but in her last two she’s gone right to the front and set the pace. For a lightly raced horse she’s shown some ability to battle in the stretch, but she’s going to have trouble getting an early lead in this field.
Five G Race Odds: 12-1
A winner on both turf and dirt, Five G was well up the track in her first lifetime start at Saratoga, but has not been worse than second in her five starts since then.
Last out she was able to take the field wire-to-wire in the (G2) Gulfstream Park Oaks, but there are some legitimate questions as to the quality of the field that day. The second-place finisher, Anna’s Promise, is a long shot here at ML odds of 30-1.
Note: Five G was scratched from the race on Thursday.
Here’s My 2025 Kentucky Oaks Free Pick.
There’s a lot of early speed in this race, with at least five or six of the 14 being the type of runners that want to be on the front end or very close to it in the early going.
As if she needs the help, that could set up perfectly for the stalking Good Cheer, and she could very well be ready to cruise to another open-lengths win.
But she’s going to be at very low odds, so I’m going to try and beat her with Quietside. Although it’s noted above the post-position draw did her no favours, I can still see her settling just off the early pace – perhaps just ahead or just behind Good Cheer – and I see those two being the ones to take over as they turn down the stretch.
I’ll pick Quietside for the win with Good Cheer in the exacta.
It’s worth noting that thunderstorms are in the forecast for Louisville on Friday and the track could come up wet. Among the field, Simply Joking, Take Charge Milady and Good Cheer all have a win on an off track. Early On, Anna’s Promise, Bless The Broken and Quietside have all been runners-up on tracks rated sloppy or muddy.
Full Field: 2025 Kentucky Oaks Odds
By post position
- #1 – Early On 30-1
- #2 – Simply Joking 10-1
- #3 – Fondly 20-1
- #4 – Drexel Hill 30-1
- #5 – Quickick 30-1
- #6 – Ballerina d’Oro 10-1
- #7 – La Cara 6-1
- #8 – Five G 12-1 (scratched)
- #9 – Tenma 12-1
- #10 – Take Charge Milady 12-1
- #11 – Good Cheer 6-5
- #12 – Anna’s Promise 30-1
- #13 – Bless The Broken 30-1
- #14 – Quietside 8-1
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