Sidney's Candy set a new track record for 5+1⁄2 furlongs (1:02.71) in his maiden win on August 22, 2009, at Del Mar. He was sent to the sidelines following the race due to sore shins. He returned to the track in an allowance race at Santa Anita on December 30 and finished fourth after hopping and stumbling at the start.
He began his three-year-old season with a victory in the seven-furlong GII San Vicente Stakes. He followed that up with a half-length victory in the 1+1⁄16-mile GII San Felipe Stakes, beating previously undefeated graded stakes winner Caracortado.
Sidney's Candy won the first Grade I of his career when he wired the field in the 2010 Santa Anita Derby, winning by 4+1⁄2 lengths under jockey Joe Talamo. It was the first Santa Anita Derby victory for Talamo and Southern California-based trainer John W. Sadler.
Sidney's Candy started in the 20th position at the 2010 Kentucky Derby.