シーザスターズ
Mastercraftsman's first race of 2009 was the English 2000 Guineas ridden by Pat Smullen. The race was won by Sea the Stars with Mastercraftsman finishing in 5th place and behind Aidan O'Brien's other runner Rip Van Winkle. Success came in the Irish version of the classic with Mastercraftsman going starting favourite and going on to win by 4 and a half lengths. A few weeks later he returned to England to win the St. James's Palace Stakes at Royal Ascot. Mastercraftsman contested the International Stakes and Irish Champion Stakes finishing 2nd and 3rd place respectively behind winner Sea the Stars. He easily won the Group 3 Diamond Stakes as odds on favourite before a trip to the Breeders' Cup. He was favourite to win his last race the Breeders' Cup Dirt Mile but could on manage 4th place behind the Kentucky Cup Classic winner Furthest Land.