He scored his 5,000th career victory on July 27, 2008 by guiding Bella Attrice to victory in the 7th race at Saratoga Race Course. In 2009, Desormeaux won the Belmont Stakes for the first time when he rode Summer Bird to victory, followed by wins in the Travers Stakes and Jockey Club Gold Cup. Desormeaux commented after the latter win, "He's trying to be the best horse I've ever ridden. He was awesome today." The wins would earn the colt the Eclipse Award for Outstanding Three-Year-Old Colt.