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.