Unbridled's Song made his racing debut on August 26, 1995 as the odds-on favorite in a maiden special weight race at Saratoga. He went to the early lead then drew off in the stretch to win "handily" by lengths. He was then stepped up to Grade I stakes company in the Champagne Stakes on October 7 in which he finished fourth behind Maria's Mon. He made his final start as a two-year-old in the Breeders' Cup Juvenile where he was the second choice in a strong field of 13. He broke poorly and experienced traffic problems on the first turn before moving into contention down the backstretch. He started his drive on the final turn and battled Hennessy down the stretch, winning by a neck in a time of 1:41:60.