The 2008–09 Chicago Blackhawks season was the 83rd season for the National Hockey League franchise that was established on September 25, 1926. Prior to the start of the season, the Blackhawks announced that 20-year-old center Jonathan Toews would serve as the team's captain for the 2008–09 season, thus making him the 3rd-youngest player to earn that distinction in the NHL. Their regular season began on October 10, 2008, against the New York Rangers and concluded on April 12, 2009, against the rival Detroit Red Wings. The Blackhawks played in the Winter Classic, an outdoor game, against the Red Wings at Wrigley Field on January 1, 2009. The team succeeded in making the 2008–09 playoffs with a 3–1 win over Nashville on April 3 after missing the 2007–08 playoffs by three points.

The 2009 NHL Winter Classic was an outdoor ice hockey game played in the National Hockey League (NHL) on January 1, 2009, at Wrigley Field in Chicago, Illinois. The second edition of the Winter Classic, it matched the Chicago Blackhawks against the defending Stanley Cup champion Detroit Red Wings in the 701st game between the Central Division rivals. The Red Wings won the game, 6–4, despite falling behind 3–1 in the first period. It was the first Winter Classic to involve at least one of the Original Six teams, and the first to feature teams from the Western Conference.