McCarron began riding in 1974, mostly racing at Bowie Race Track in Maryland and Penn National in Pennsylvania. In 1974 he won the Eclipse Award as the best jockey of the year.

In 1975, McCarron led in victories with 648. In 1977 McCarron again led in victories with 405 and money won with $7,663,300 to claim his second Eclipse Award.

In 1981, 1984, 1991 and 1994 McMcarron was the top money winner and in 1983, he became the youngest jockey ever to achieve both $50 million in career earnings and more than 3 thousand wins.

McCarron won nine Breeders' Cup races, including five Breeders' Cup Classics and rode six winners in the U.S. Triple Crown Races:

1. Kentucky Derby – Alysheba (1987), Go for Gin (1994)
2. Preakness Stakes – Alysheba (1987), Pine Bluff (1992)
3. Belmont Stakes – Danzig Connection (1986), Touch Gold (1997)

Through 2003, McCarron ranks sixth all-time with 7,139 wins and third in earnings with $264,380,651.

In 1989 Chris McCarron was inducted into the National Museum of Racing and Hall of Fame. After 28 years in racing he retired in June 2002. He finished as thoroughbred racing's all-time leader in purse earnings with more than $264 million in winnings.

In 2003, McCarron served as a technical advisor, racing designer and actor in the 2003 film Sea biscuit. That same year he was hired by Magna Entertainment Corp. to serve as Vice President and General Manager of Santa Anita Park. In July 2005 McCarron announced he would be opening the first riding academy in Lexington Kentucky.