5 of the toughest Kentucky Derby prep race wins

Each year, 20 horses have the once in a lifetime chance to win the Run for the Roses. To earn a place in the starting gate they must compete in the Road to the Kentucky Derby, a qualifying series of races at tracks across the country and around the world. Points are awarded to the top five finishers in each. This year, 36 Derby prep races were held in the U.S. Here is a look at five of the toughest wins on the 2024 Derby trail.  

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The Remsen S. (G2), Dec. 2 at Aqueduct

Dornoch, full brother to last year’s Kentucky Derby winner Mage, took the early lead in his first Derby prep and held it until the final stretch. Sierra Leone made a dramatic comeback from last to surpass him, and Dornoch seemed beat. But Dornoch re-rallied at the wire in an exhilarating photo finish to beat Sierra Leone, the horse with a $2.3 million purchase price at auction. 

In their next races, Dornoch triumphed in the Fountain of Youth (G2), and Sierra Leone was victorious in the Risen Star S. (G2). The rivals met again in the Blue Grass S. (G1) as Sierra Leone rolled from the back of the pack again and won. Dornoch finished fourth, but the Remsen proves he is still a strong contender.

The Holy Bull S. (G3), Feb. 3 at Gulfstream

Fierceness became the early Kentucky Derby favorite after winning the Breeders’ Cup Juvenile (G1) by an astounding 6 1/4 lengths. All eyes were on him as he made his sophomore debut in the Holy Bull S. But it was not his day. He had a rough start and never recovered, finishing third behind Hades, who later made an appearance in the Lexington S. (G3), coming in seventh.  

Fierceness’s favorite status may have been questioned, but he quickly rebounded in the Florida Derby (G1) with a 13 1/2 romp, making him a likely top choice May 4. 

The Risen Star S. (G2), Feb. 17 at Fair Grounds

The penultimate race on the Louisiana Road to the Derby was a springboard for some of the top contenders in the 150th Kentucky Derby. Sierra Leone arrived ready, and won by half a length over Track Phantom, winner of the first two Fair Grounds preps. 

The third and fourth place finishers returned to win 100-point races: Catching Freedom in the Louisiana Derby (G2) and Resilience in the Wood Memorial (G1), respectively. Honor Marie, fifth, was redeemed with a second in the Louisiana Derby. All are expected to compete on the first Saturday in May. 

The Santa Anita Derby (G1), April 6 at Santa Anita Park

Trainer Bob Baffert has won a 100-point prep race a record of nine times. It looked like even-money favorite Imagination might become the tenth. Frankie Dettori, his jockey, was having a massive day: he won six consecutive races on the undercard, including the Santa Anita Oaks (G2). However, second-choice Stronghold outdueled the favorite to the wire to win by a neck. 

Stronghold will be the first Derby starter for trainer Philip D’Amato, jockey Antonio Fresu, and breeders/owners Eric and Sharon Waller. 

The Lexington S. (G3), April 13 at Keeneland

The final race on the Road to the Kentucky Derby offered a potential path to the Run for the Roses to three horses: Holy Bull S. (G3) winner Hades, John Battaglia Memorial S. winner Encino, and Southwest S. (G3) third place finisher Liberal Arts. 

A victory would have locked in a spot for Hades, or grant entry to Encino or Liberal Arts if any of the top twenty decided not to compete. Encino was up to the challenge: he wired the field, digging in to win by 3/4 of a length. After defections from the top twenty, Encino now has a spot as a Kentucky Derby contender.