Leparoux had a career best year in 2009, capped by wins in the Breeders' Cup Dirt Mile on Furthest Land, the Filly & Mare Sprint on Informed Decision and the Juvenile Fillies on She Be Wild. He won the Shoemaker Award as the winningest jockey at the 2009 Breeders' Cup, being only the 2nd jockey in history to win three Breeders' Cup races in a single year, following Garrett Gomez. He led the North American earnings list and received the Eclipse Award for Outstanding Jockey in 2009. He was only the fourth jockey to win Eclipse Awards as both an apprentice and journeyman.