2023 Kentucky Oaks winner: Pretty Mischievous (10-1) wins the 149th Kentucky Oaks

Breaking from the far outside post position in a 14-horse field didn’t stop Pretty Mischievous from springing a 10-1 upset in the Friday’s 149th running of the $1.25 million Kentucky Oaks (G1) at Churchill Downs.

Pretty Mischievous endured a wide trip under jockey Tyler Gaffalione while settling in fifth position behind early fractions of :23.07 and :46.96 set by Flying Connection. But Pretty Mischievous advanced steadily around the far turn, seized the lead at the top of the stretch, and held off a late charge from Gambling Girl to prevail by a neck, completing 1 1/8 miles in 1:49.77.

Gambling Girl pulled clear of third-place finisher The Alys Look, followed by stretch-running favorite Wet Paint, Dorth Vader, Flying Connection, Defining Purpose, Mimi Kakushi, Wonder Wheel, Southlawn, Affirmative Lady, And Tell Me Nolies, Botanical, and Promiseher America.

A crowd of 106,381 attended the historic race, which has been contested every year since 1875.

A Godolphin homebred trained by Brendan Walsh, Pretty Mischievous is a daughter of four-time leading North American sire Into Mischief out of the Tapit mare Pretty City Dancer, a classy runner who won the 2016 Spinaway (G1) at Saratoga.

Pretty Mischievous returned $22.74 to win, $10.10 to place, and $7.40 to show. Gambling Girl paid $12.84 to place and $8.36 to show, while The Alys Look triggered the biggest show payoff at $13.80. (All payoffs based on $2 bets.)

Bettors who solved the $2 exacta picked up $403.14. The 50-cent trifecta paid $1,997.14, the $1 superfecta $15,391,09, and the $1 Super High 5 $111,346.02.