LOUISVILLE, KY (Friday, May 5, 2023) –  Godolphin’s homebred Pretty Mischievous held off a late charge from Gambling Girl by a neck to win the 149th running of the $1.25 million Longines Kentucky Oaks (GI) for 3-year-old fillies at Churchill Downs before a crowd of 106,381 on a sun-splashed afternoon.

Finish Line Photo of Pretty Mischievous

Photo provided by Churchill Downs/Coady Photography

Trained by Brendan Walsh and ridden by Tyler Gaffalione, Pretty Mischievous completed the mile and one-eighth over a fast main track in 1:49.77. It is the first Kentucky Oaks victory for Walsh and Gaffalione.

The victory was worth $767,250 and increased Pretty Mischievous’ earnings to $1,268,560 with a record of 7-5-1-1.

Pretty Mischievous is a Kentucky-bred daughter of Into Mischief out of the Tapit mare Pretty City Dancer.

Pretty Mischievous, Photo provided by Churchill Downs/Coady Photography

Flying Connection led the field of 14 through fractions of :23.07, :46.96 and 1:11.28 with Defining Purpose to her outside and Dorth Vader three wide just behind the leader.

Gaffalione had Pretty Mischievous in the clear four wide and launched his bid on the far turn with a four-wide move that propelled her to the front at the top of the stretch.

Pretty Mischievous opened up on the field and had enough left in the run to the wire to hold off Gambling Girl, who had rallied from far back.

Pretty Mischievous debuted here last September with a 2 ¼-length victory sprinting 6 ½ furlongs and followed that up with an allowance victory going seven furlongs.

This winter at Fair Grounds, she won the Untapable Stakes and Rachel Alexandra (GII) before finishing second in the Fair Grounds Oaks (GII).

Pretty Mischievous returned $22.74, $10.10 and $7.40. Gambling Girl, under Irad Ortiz Jr., returned $12.84 and $8.36 and finished 2 1/2 lengths in front of The Alys Look, who paid $13.80 to show under Javier Castellano.

It was another neck back to favored Wet Paint, who was followed in order by Dorth Vader, Flying Connection, Defining Purpose, Mimi Kakushi, Wonder Wheel, Southlawn, Affirmative Lady, And Tell Me Nolies, Botanical and Promiseher America.