Skippylongstocking

Skippylongstocking (foaled April 2, 2019) is an American Thoroughbred racehorse. He is best known for winning the Grade 1 Pegasus World Cup Invitational in 2026.

Skippylongstocking is a bay horse bred by Brushy Hill, LLC.^[2] He is sired by Exaggerator, out of a War Chant mare named Twinkling. Skippylongstocking was sold as a yearling at the 2021 Spring Sale of Two-Year-Olds in Training for $37,000 to Daniel Alonso.^[3][4]

Skippylongstocking started his career at Gulfstream Park, breaking his maiden on his third attempt before starting in the Street Sense Stakes, where he finished fourth.^[5][6] By placing 3rd in an December allowance race at Gulfstream, Skippy finished his juvenile campaign with a 1-1-1-2 record in five starts.

During Skippylongstocking's three-year-old season, he won the Harlan's Holiday Stakes^[7] and the West Virginia Derby^[8], along with 3rd place efforts in the Wood Memorial and Belmont Stakes. For the season his record was 3-0-2-1 in nine starts, with $724,310 total earnings.

With six graded-stakes starts, Skippy's four-year-old record was 2-1-1; with wins in the Challenger Stakes and Charles Town Classic, 2nd in the Cornhusker Handicap,^[9] and 3rd in the Breeders' Cup Dirt Mile for $816,375 in total earnings.

Skippy had an unfortunate start to his five-year old season with a DNF in the Pegasus World Cup, albeit walking off.^[10] He would return two months later with a repeat win in the Challenger Stakes ^[11] followed by a win in the Oaklawn Handicap;^[12] marking his first time winning two stakes in-a-row. Skippy placed 3rd in the Stephen Foster and 5th in the Whitney before a repeat victory in the Charles Town Classic. In his last two starts Skippy placed 2nd in the Woodward Stakes and 6th in the Breeders' Cup Dirt Mile, finishing with a 3-1-1 record in 8 graded-stakes starts and $1,498,800 in total earnings.

Skippy's six-year-old campaign was highlighted by a 3-peat win in the Challenger Stakes ^[13] and capturing the Hollywood Gold Cup^[14]. Although he was unable to defend his Charles Town Classic title, Skippy won his second Harlan's Holiday Stakes to finishing the season 3-0-2 in 7 graded-stakes starts with $682,265 in total earnings.

Skippy finally got his first Grade 1 score by winning the 2026 Pegasus World Cup ^[15], his fourth consecutive start in the race. The win gave him at least one victory in every grade; 1 - GI , 4 - GII, 6 - GIII.