competing in 2005, his performances that year, capped off by a win in the fall's breeders' cup juvenile, earned him the eclipse award for outstanding 2-year-old male horse. going into the 2006 racing season he was expected to be a contender for the u.s. triple crown. however, on february 7, 2006, it was announced that stevie wonderboy had suffered a hairline fracture in his ankle. on february 8, a screw was inserted into his leg to correct the fracture. the announcement was made that he would not race in the kentucky derby or any of the triple crown races. in july 2007, it was announced that stevie wonderboy had retired.