English horseman Michael Tabor purchased Left Bank as a two-year-old for $600,000 at a February 1999 Fasig-Tipton sale at Calder Race Course.
He first beat the betting favorite Squirtle Squirt to capture the September 22 Vosburgh Stakes at Belmont Park, clocking the second-fastest time in the race's 62 year history.
Then, on November 24 at Aqueduct Racetrack, Left Bank won the Cigar Mile Handicap by defeating top-rated challengers, Graeme Hall and Red Bullet.
[4] After his win in the Whitney, Left Bank was being prepared to run in the Woodward Stakes at Belmont Park but suffered another attack of colic.
Left Bank posthumously earned the Eclipse Award when he was voted the 2002 American Champion Older Male Horse.