2000: Three-year-old season

Recovered, Left Bank was able to race the following year notably winning the 2000 Discovery Handicap at New York's Aqueduct Racetrack.

2001: Four-year-old season

At age four in 2001, Left Bank got off to a slow start but in the fall won two Grade 1 races. 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.

2002 Championship year and death

Rested since his win in November's Cigar Mile, Left Bank began his five-year-old campaign on May 12, 2002 with a win in the Grade 3 Bold Ruler Handicap. After a poor showing in the May 27 Metropolitan Handicap, on July 4 Left Bank set a Belmont Park track record for seven furlongs in winning the Grade 2 Tom Fool Handicap by six and a quarter lengths. Moving up from sprint race distances, Left Bank followed his record-setting win in the Tom Fool by equaling the Saratoga Race Course track record for 1⅛ miles (9 furlongs) in his victory in the Grade 1 Whitney Handicap.

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. On August 10, 2002 the horse was rushed to the equine hospital at Tufts University near Boston, Massachusetts where he underwent emergency surgery. Following his surgery, Left Bank was sent to recover at Ashford Stud in Versailles, Kentucky but had to undergo further operations from which he was unable to recover and died on October 7, 2002.