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.

Background

Skippylongstocking is a bay horse bred by Brushy Hill, LLC. 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.

Racing career

2021: Two-year-old season

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. 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.

2022: Three-year-old season

During Skippylongstocking's three-year-old season, he won the Harlan's Holiday Stakes and the West Virginia Derby, along with third-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.

2023: Four-year-old season

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, and 3rd in the Breeders' Cup Dirt Mile for $816,375 in total earnings.

2024: Five-year-old season

Skippy had an unfortunate start to his five-year old season with a DNF in the Pegasus World Cup, albeit walking off. He would return two months later with a repeat win in the Challenger Stakes followed by a win in the Oaklawn Handicap; 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.

2025: Six-year-old season

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

2026: Seven-year-old season

Skippy finally tallied his first Grade 1 by winning the 2026 Pegasus World Cup, his fourth consecutive start in the race. The win gave him at least one victory in every stakes grade. In March Skippy posted a dominant win in the Essex Handicap and became the eighth horse to win both the Essex and Oaklawn handicaps (albeit in different years).

Pedigree