In December 2000, Winchester participated in the World Junior Hockey Championship with the United States, finishing in fourth position.

Winchester made his professional debut in the 2003–04 American Hockey League season, playing for Edmonton's farm affiliate, the Toronto Roadrunners.

Winchester split 2005–06 between the Oilers and the Hamilton Bulldogs, going scoreless during the NHL regular season but scoring the game-winning goal in his playoff debut, the second game of a series with the number one seeded Detroit Red Wings.

On June 26, 2007, the Oilers declined to make Winchester a qualifying offer, which allowed him to become an unrestricted free agent as of July 1, and on the 6th, he signed with the Dallas Stars.

[4] A free agent through the duration of the 2012–13 NHL lockout, Winchester accepted a try-out to the Calgary Flames training camp once the dispute was resolved on January 12, 2013.