2025 Kentucky Oaks Predictions and Recommended $100 Wager

by Joey House - 5/1/2025

With the 151st Kentucky Derby on the horizon, the 2025 Kentucky Oaks on May 2 lights up Churchill Downs as the ideal opening act for the weekend's racing extravaganza. This Grade 1 stakes race, boasting a $1.25 million purse, showcases America's finest three-year-old fillies vying for the cherished garland of lilies. Far from a mere warm-up, the Oaks commands attention, highlighting rising stars and seasoned trainers poised to foreshadow the Derby's intensity. In its 151st running, the Kentucky Oaks is set to launch the Derby weekend with a captivating burst of racing glory.

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History of the Oaks

Since its founding in 1875 by Meriwether Lewis Clark Jr. at Churchill Downs, the Kentucky Oaks has reigned as America's premier race for three-year-old fillies, inspired by England's Epsom Oaks and becoming a cornerstone of Derby weekend. The race's iconic garland of lilies, introduced in 1896 and made official with Star Gazer lilies in 1991, earned it the loving nickname "Lilies for the Fillies." Run initially at 1½ miles, the Oaks settled at its current 1⅛-mile distance in 1982. It has since showcased horse racing brilliance through stars like Davona Dale, Monomoy Girl, and Rachel Alexandra, who in 2009 stormed to a record 20¼-length victory. Elevated to permanent Grade 1 status in 1991 to properly reflect its elite caliber, the Kentucky Oaks, now with a $1.25 million purse, continues to captivate fans each spring as a thrilling prelude to the Kentucky Derby.

2025 Kentucky Oaks Field

This year's Oaks lineup boasts a highly competitive field, featuring nine entries that triumphed in their previous races. With such impressive success, there will likely be enticing odds on the winning horses. Here are my top five contenders for Friday's main event.

PP 3. Fondly, 20-1. Fondly remains unbeaten since starting her career in February with a seven-furlong maiden win at Tampa Bay Downs. Trainer Graham Motion guided her to the Oaks trail, where she claimed the Virginia Oaks, holding the lead throughout the one-turn 1 1/16-mile race. Jockey Irad Ortiz Jr. continues to ride her.

PP 7. La Cara, 6-1. La Cara is one of two Grade 1 winners in the Oaks field, having captured the Ashland (G1) with a front-running performance against eight rivals at Keeneland. On her path to the Oaks, she also secured victories in the Pocahontas (G3) at Churchill Downs and the Suncoast at Tampa Bay Downs.

PP 9. Tenma, 12-1. Tenma has five career wins, including her last three in California graded stakes. She dominated her last two races with stalking tactics as the odds-on favorite. She also won the Grade 1 Del Mar Debutante in September. Trainer Bob Baffert has three Oaks wins with Abe Tasman in 2017, Plum Pretty in 2011, and Silverbulletday in 1999.

PP 11. Good Cheer, 6-5. Good Cheer is undefeated, winning all six of her races, four of which came last year. Her speed figures have steadily risen, placing her among the fastest in the field. Her victories have ranged from 2 ½-lengths to 17. She has faced only three of the Oaks field's fillies in her races. Trainer Brad Cox won the Oaks with Shedaresthedevil in 2020 and Monomoy Girl in 2018.

PP 14. Quietside, 8-1. Quietside has never finished outside the top three in seven races. Her last five starts, all on the Oaks trail, included pace-pressing wins in the Honeybee and the Fantasy in February and March. Jockey Jose Ortiz, riding at the peak of his career, has drawn her best performances.

Recommended $100 Wager

While betting win/place/show is the safest route, my wagers on major stakes races tend to be more daring than my daily plays. With that in mind, I will play a $1 Key Box of 14-Quietside with 3,6, 7,9,11. I try not to choose a heavy favorite, such as the #11 Good Cheer, because I'm not blown out of the water if an upset occurs. By putting them in the rest of the little group I pick, I can win if the favorites do come through or falter. All I need is my key horse to finish in the top three and two of my other selections. I've hit some very nice wagers this way. This method costs $60, so I still have $40 to play with. For $30, I'm making a $5 Exacta Box of 7,11,14, and I'm putting my final $10 on 11-Quietside to win.

$1 Key Box: 14 with 3,6,7,9,11 = $60

$5 Exacta Box: 7,11,14 = $30

$10 Win: 11 = $10

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Most Recent Kentucky Derby Picks and Predictions

Pick:	Inter Milan -1.5 (-180)
Start:	June 21, 2025 @ 3:00 PM
Expert:	Doc's Sports

Analysis:

Doc’s Sports Free FIFA Club World Cup Soccer Play. Take Inter Milan -1.5 (-180) over Urawa Red Diamonds (3 p.m. EST, Saturday June 21) (Graded after regulation time - 90min - plus injury time – we need Inter Milan to win by two goals) Urawa Red Diamonds got beat 3-1 in their opener by Argentinian side River Plate, and they take a big step up in competition today against the Champions League runner up in Internazionale. The Italian side played to a 1-1 draw over Mexican side Monterrey in their first match. That was a very disappointing result, especially following their embarrassing 5-0 loss in the Champions League final recently. So, Inter needs a win here. And they need it big. They are now in a precarious position after gaining only a point in their opener, so they know they might need goals for a tiebreaker down the line. Their coach urged the side to be aggressive in this matchup, and this feels like it could be a three- or four-goal win. Inter have some injury concerns, but they have enough quality to get the job done here with style points. This is a lot of juice to lay in this match, but we think this is a safe bet today. Read More Read Less