Skippylongstocking

Skippylongstocking earned his first career win in his third career start at Gulfstream Park, getting the job done Sept. 26, 2021, with a 10 ½-length runaway victory going a mile on the dirt main track. He subsequently ran fourth at Churchill Downs before an unplaced finish at Gulfstream in his final start as a 2-year-old.

The Exaggerator colt was sixth in the Mucho Macho Man Stakes at Gulfstream in his 3-year-old bow on Jan. 1, 2022, beaten by 17 ¾ lengths by Simplification. Two starts later he regained his winning form with a 3 ¾-length allowance win going 1 1/8 miles at Gulfstream Park.

Sent to New York for the $750,000 Wood Memorial Stakes Presented by NYRA Bets April 9 at Aqueduct, Skippylongstocking finished willingly for third in his graded stakes debut to earn 20 points toward qualifying for the Kentucky Derby Presented by Woodford Reserve.

Skippylongstocking skipped the Derby and raced next in the Grade 1 Preakness Stakes at Pimlico on May 21. He finished fifth by 7 1/2 lengths after a wide trip.

Following the Preakness, Skippylongstocking bounced back next out with a third-place performance in the Grade 1 Belmont Stakes Presented by NYRA Bets at Belmont Park on June 11. 

In his first start after the Belmont, Skippylongstocking broke through with his first graded stakes win, out-dueling Belmont fourth-place finisher We the People to take the Grade 3 West Virginia Derby at Mountaineer Park by 1 ½ lengths on Aug. 6. Following the career milestone of the first lifetime graded stakes win, his subsequent outing was highly disappointing. Skippylongstocking finished ninth out of 11 in the Grade 1 Pennsylvania Derby at Parx on Sept. 24.

Skippylongstocking was not quite done for the year 2022, however, he had one more start in him and it came in Dec. 31 in the Grade 3 $150,000 Harlan's Holiday Stakes at Gulfstream Park. Skippylongstocking pressed the pace throughout and took over in the stretch to draw off to a two-length win, going the 1 1/16 miles in a time of 1:42.76.  The race was a prep for the $3 million Pegasus World Cup four weeks later, when Skippylongstocking faded after a mild bid and was unplaced. 

Skippylongstocking regained his top for March 11 at Tampa Bay Downs as the odds-on favorite in the $100,000 Michelob Ultra Challenger Stakes, settling just off the pace in the 1 1/16-mile race and surging clear to a dominant win in the stretch under Irad Ortiz Jr.

After an unplaced finish as the favorite in the Grade 3 Ben Ali Stakes in April at Keeneland, Skippylongstocking finished second by three-quarters of a length in the Grade 3 Prairie Meadows Cornhusker Handicap in July. He returned to the winner’s circle in his next start when dominating on a wet-fast track in the $1 million Charles Town Classic, leading from start to finish in a five-length romp Aug. 25. 

Skippylongstocking finished his 2023 campaign with a third-place finish in the BigAss Fans Breeders' Cup Dirt Mile on Nov. 4 at Santa Anita, where he was only 3 3/4 lengths behind 2023 Horse of the Year Cody's Wish and Preakness Stakes winner National Treasure.

Skippylongstocking returned for his 5-year-old season in 2024 and started it off on Jan. 27 in the Grade 1 Pegasus World Cup, where he failed to finish. For his next race, Skippylongstocking chose to try to gain some momentum in the same race he used the year before in the $100,000 Michelob Ultra Challenger Stakes at Tampa Bay Downs on March 9. He was successful in his effort to rediscover the winner's circle, winning the 1 1/16-mile Grade 3 race by 2 1/2 lengths.

Skippylongstocking earned one of the biggest wins of his career in this next start, which was a victory in the Grade 2, $1.25 million Oaklawn Handicap going 1 1/8 miles at Oaklawn Park on April 20, where he convincingly topped an 11-horse field as the 8-5 favorite on the tote board. He subsequently finished third in the $1 million Stephen Foster Stakes and fifth in the $1 million Whitney before returning to the winner’s circle with a front-running, 5 3/4-length runaway victory in the $1 million Charles Town Classic Stakes Aug. 23, his second consecutive win in that race.

Skippylongstocking wrapped-up 2024 with a runner-up finish in the Grade 2 Woodward Stakes at Belmont at the Big A on Sept. 28 and then a sixth-place finish in the BigAss Fans Breeders' Cup Dirt Mile at Del Mar. 

Skippylongstocking kicked off his 6-year-old season in 2025 with a competitive third-place finish in the $3 million Grade 1 Pegasus World Cup Invitational Stakes on January 25 at Gulfstream Park. Just as he had done before, Skippylongstocking made a March trip to Tampa Bay Downs to get back into the winner's circle and was successful when taking the Grade 3 $100,000 Michelob Ultra Challenger Stakes going 1 1/16 mile atop a field of four horses on March 8. 

Skippylongstocking next went to Oaklawn Park where he attempted to defend his title in the Grade 2 Oaklawn Handicap but settled for third.

Skippylongstocking was back to his best again in his following start when he showed he still had what it takes as a 6-year-old with a victory atop a seven-horse field in the Grade 2 $200,000 Hollywood Gold Cup going 1 1/4 miles at Santa Anita on May 26. Sent off as the 4-5 favorite, Skippylongstocking stalked the pace in mid-pack, moved up to challenge turning for home, assumed a short lead in the stretch and could not be denied when victorious by three-quarters of a length in a time of 2:01.64.

The next trip to the winner's circle for Skippylongstocking came at Gulfstream Park on Dec. 20 when he was victorious in the Grade 3 $150,000 Harlan's Holiday Stakes where he prevailed by a head over Poster as the 2.40-1 second choice in a seven-horse field. The win was the second Harlan's Holiday Stakes title of veteran Skippylongstocking's career.

The Harlan's Holiday Stakes victory propelled Skippylongstocking to a start in the Grade 1 $3 million Pegasus World Cup Invitational Stakes for his next outing in the first start of his 7-year-old season on Jan. 24, 2026, at Gulfstream Park. The Pegasus World Cup then turned into the standout victory in Skippylongstocking's storied career when he topped and 12-horse field with a come-from-behind upset win by a 1 3/4-length margin under jockey Tyler Gaffalione. The $1,686,000 winner's share of the purse raised Skippylongstocking's career earning up over the $5 million mark. The Pegasus also was a qualifying race for the 2026 Longines Breeders' Cup Classic, guaranteeing him a spot in the starting gate in the fall.

Skippylongstocking's winning start to the 2026 racing season continued in his next outing when he won again in the Grade 3 $500,000 Essex Handicap going 1 1/8 miles at Oaklawn Park on March 21 when he easily topped a seven-horse field by 5 1/4 lengths as the 1.10-1 favorite. His two-race winning streak in 2026 came to an end in the May 1 Alysheba Stakes Presented by U.S. Army, as Skippylongstocking battled gamely through the stretch and bumped with rival Corporate Power before finishing a neck back in second. Jockey Tyler Gaffalione’s claim of foul was rejected.