Casually Crafting an Oaks-Derby Double

The Kentucky Oaks/Kentucky Derby double offers bettors a unique two-day challenge, asking them to pick the winners of both the Kentucky Oaks (G1) on Friday and the Kentucky Derby (G1) on Saturday.

Linking these spring tests of sophomores at the highest level, the wager creates a high-stakes narrative that serves as the ultimate test of handicapping skill, rewarding those who can identify the most dominant three-year-olds in the country across two historic races at Churchill Downs.

What Is the Oaks-Derby Double?

This bet asks you to select at least one horse to win the Kentucky Oaks and at least one to win the Kentucky Derby. The wager starts at $1 and goes up from there, so you have flexibility with the amounts you would like to risk. Picking horses for a two-race bet 24 hours apart might feel like a tall task, but even these full fields, with 34 horses between them, have a few horses that stand above the rest and make great candidates for your Oaks-Derby Double. 

First, let’s look at a couple of fillies who fit the bill. 

Who Will Wear the Lilies?

A daughter of Honor A.P., who was fourth in the 2020 Kentucky Derby, Counting Stars has the necessary tools in both experience and pedigree to make the nine furlongs of the Kentucky Oaks a winning trip. Her sire had no trouble beating eventual Kentucky Derby winner Authentic in a COVID-delayed Santa Anita Derby (G1) at the Oaks’ distance. Counting Stars is the first foal of Paynterbynumbers, who won at both a mile and 1 1/16 miles. 

Even better, Counting Stars has a win over the Churchill Downs surface, taking her 6 1/2-furlong debut by four lengths. Her three stakes wins have all come at Oaklawn Park, including a 5 1/2-length victory over Search Party, a fellow Mark Casse trainee and Oaks starter in the Grade 2 Fantasy at 8 1/2 furlongs, just a sixteenth shorter than the Run for the Lilies. She faced Explora in the Grade 3 Honeybee and was just three-quarters of a length back of the Bob Baffert trainee and fellow Oaks starter. With seven lifetime starts, Counting Stars has the experience not only over Churchill’s racing surface, but also the seasoning needed to handle this biggest of stages. 

Named for the late Percy Pool, a bartender at Keeneland and Churchill Downs, Percy’s Bar is a filly on the rise. She won her lone start of 2026, the Ashland (G1) at Keeneland, by 2 3/4 lengths over Zany. The Ashland was her first Grade 1 win in four tries, though she was victorious by the same margin in the 2025 Alcibiades (G1) before being disqualified for interference. Her first stakes win came back in late June 2025 at Churchill Downs, where she won the six-furlong Debutante S. by five lengths.

In addition to her experience over the Churchill Downs surface as well as her multiple in-the-money finishes at the Grade 1 level, her pedigree offers some steady influence at nine furlongs. Her sire Upstart won the Razorback H. (G3) and the Holy Bull (G2) at 1 1/16 miles, and damsire Super Saver was victorious at 1 1/4 miles in the 2010 Kentucky Derby. The Oaks is an extra 330 feet beyond her experience at 1 1/16 miles, but Percy’s Bar seems up to the challenge.

Who Wants the Roses?

Bred by Jack Oxley, who lifted the Kentucky Derby trophy himself with Monarchos in 2001, Further Ado enters the gate on Saturday with the potential to give sire Gun Runner his first Derby winner and the Oxleys their first win as breeders. It took him three tries to break his maiden last fall, getting his first win at Keeneland before taking the Kentucky Jockey Club (G2) at Churchill Downs. He then won two of his next three, finishing second to The Puma in the Tampa Bay Derby (G3) and then flashing brilliance in his 11-length Blue Grass (G1) victory. That recent form and the presence of three-time Kentucky Derby-winning John Velazquez make Further Ado an appealing win contender.

Besides being a sentimental favorite for many, So Happy’s turn in the Santa Anita Derby shows why he belongs among the 20 on the first Saturday in May. He entered the race with two wins in three starts and then turned the tables on Potente, who beat him in the San Felipe (G2), at the top of Santa Anita’s stretch, dueling with his fellow Derby starter briefly before pulling away to win by 2 3/4 lengths. By Runhappy, So Happy may appear to have distance limitations on the surface, as his sire is a champion sprinter, but Runhappy is by Super Saver, the same horse that is the damsire of Percy’s Bar, and his dam gets stamina influence from Blame, who famously defeated Zenyatta in the 1 1/4-mile Breeders’ Cup Classic (G1). Even better, So Happy gets the services of Hall of Fame jockey Mike Smith, who won the Derby with Giacomo in 2005 and then the Triple Crown with Justify in 2018. So happy to endorse So Happy for this double. 

The Bet – (4) Counting Stars, (11) Percy’s Bar/(8) So Happy, (18) Further Ado

Without further ado(!), let’s count our stars and construct an Oaks-Derby double with those four horses. At $1, this double combination costs $4 and pays out between $55 and $220. 

Bumping the bet up to $5, the combination then costs $20, but the increased payouts offset that cost considerably, from a minimum of $275 to a maximum of $1,100 if Counting Stars and So Happy score in these classic races.