Bred in Kentucky by Sanford Robertson, Eskendereya was a $250,000 Keeneland September purchase.

Eskendereya made his career debut on turf at Saratoga, rallying from off the pace to finish second.

On February 20, 2010, Eskendereya took the lead entering the final turn and pulled away for an 8½-length victory in the Grade II Fountain of Youth Stakes, beating favorite Buddy's Saint.

On April 3, 2010, Eskendereya won the Wood Memorial Stakes by 9¾ lengths, essentially repeating his dominating performance in Florida.

However, it was announced on April 25 that Eskendereya would be pulled out of the Kentucky Derby after he sustained a leg injury.