As a five-year-old, in March 2010, Icabad Crane won the Kings Point Handicap at Aqueduct Racetrack at one and one eighth miles on the dirt in 1:50.

He next finished second to Grade I winning Giant Moon by a neck in the July 26, 2010, Evan Shipman Handicap at 1-1/8 miles on the dirt at Saratoga Race Course.

On Thanksgiving Day, November 25, 2010 Icabad Crane finished second again in the Tinchen's Prince Stakes at one mile on the dirt at Aqueduct.

In the final start of his four-year-old season, he won the Alex M. Robb Stakes over Aqueduct’s inner track on New Year's Eve, December 31, 2010.

At age six, Icabad Crane won the February 17, 2011, G'day Mate Stakes at a mile and seventy yards on the Inner Dirt Track at Aqueduct Racetrack over a field of six in 1:43.63 by 2-1/4 lengths as the favorite.

In May 2011, on the Preakness Stakes undercard, he ran in the grade three $100,000 William Donald Schaefer Handicap at one and one sixteenth miles at Pimlico Race Course on conventional dirt.