Jackson Bend started his career with five wins in his first six races, including four stakes races all carded at Calder Race Course: the In Reality Stakes at 8½ furlongs, the Frank Gomez Memorial Stakes, the Affirmed Stakes at seven furlongs, and another six-furlong sprint in the Dr. Fager Stakes.
Three-year-old season
In January 2010, Jackson Bend finished second in the grade threeHoly Bull Stakes at Gulfstream Park at a mile on the dirt. In February, he was second in the Grade IIFountain of Youth Stakes at a mile and one eighth at Gulfstream behind Eskendereya. In April, he stepped up in class and ran second again to Eskendereya in the Grade I $750,000 Wood Memorial Stakes at Aqueduct Racetrack in New York at a mile and an eighth. After five wins and three graded-stakes placings, owner Robert LaPenta and trainer Nick Zito ran him in the second jewel of the Triple Crown, the $1,000,000 Preakness Stakes a Grade I at Pimlico Race Course at a mile and three sixteenths on dirt. Jackson Bend broke well and stalked the leaders in third behind First Dude and Kentucky Derby winner Super Saver passing the grandstand for the first time. He continued in third along the rail down the backstretch. Around the final turn, Eclipse Champion Lookin At Lucky and Caracortado passed him on the outside. Coming down the lane, Jackson Bend swept across five paths to the outside, passing Super Saver and Caracortado. In the final 1/16 of a mile, he continued to close on the leaders and finished third by less than a length to winner Lookin At Lucky, finishing a nose behind second-place First Dude.
On January 14, 2012, Jackson Bend won the one-mile Hal's Hope Stakes at Gulfstream Park. Under jockey John Velazquez, he was angled out in the stretch drive and scored by one length over Sangaree. In April 2012, Jackson Bend won the $400,000 Grade 1Carter Handicap at seven furlongs at Aqueduct Racetrack. As the longest shot on the board, he held off odds-on favorite Caleb's Posse to win by a nose. Preakness Stakes winner Shackleford finished another length back in third. On May 28, 2012, Jackson Bend competed in what many analysts called the strongest field assembled all year in the $750,000 Grade 1 Metropolitan Handicap. He finished fifth of six to Preakness Stakes winner Shackleford and Breeders' Cup Dirt Mile winner Caleb's Posse.