The league was created in 2003 on the premise that local teams should have local players. The existing senior league at the time, the Hanover-Taché Hockey League, included a large number of imported players. During its first season, the CSHL was operated as an independent league and did not have accreditation from Hockey Manitoba. Three teams competed that season with Mitchell winning the championship. In its second season, the CSHL was accepted by Hockey Manitoba. The league doubled to six teams, with the Grunthal Red Wings, St. Adolphe Hawks and Steinbach Huskies being accepted. Mitchell once again won the championship. Prior to the third season, the rival HTHL folded, and two teams joined the CSHL: the La Broquerie Habs and St. Malo Warriors. This brought the league total of teams to eight. The La Broquerie Habs defeated the Ste Anne Aces in four-straight games to claim the league championship. In its fourth season, the Steinbach Huskies went on hiatus while the Landmark Dutchmen folded, leaving the league with six teams yet again. The La Broquerie Habs defeated Ste. Anne in five games to claim their second straight league title. In provincial competition, the La Broquerie Habs won the Manitoba Senior 'A' provincial championship. The Steinbach Huskies rejoined the league for the 2007-08 season, while Grunthal Red Wings went on hiatus. This season produced a new champion, the Ste. Anne Aces, who defeated St. Malo in seven games to become the champions. The following season, it was the St. Malo Warriors that ended a 21-year championship drought and captured their first CSHL title. The final was a rather quick series as St. Malo won in five games, winning the cup at home against the Ste. Anne Aces. The 2008-09 season was a special year for hockey in St. Malo as both the Senior Warriors and the Junior 'B' Warriors of the Keystone Junior Hockey League captured their respective titles in the same year for the first time in the town's history. In 2009-10 season, the Steinbach Huskies won both the CSHL championship and the Manitoba Provincial 'A' Championship. The Huskies followed up their provincial championship by defeating La Broqerie in the seventh game of the finals the following day. Captain Mike Martens scored with 3:13 left in the third period to clinch the victory. The championship was a first for the Steinbach team in the CSHL, and the first local league title since the Huskies won the Hanover-Tache Hockey League in 1993-94. The Huskies repeated as champions the following season. In only their second season in the CSHL, the Niverville Clippers captured their first league title in 2012, sweeping La Broquerie in four games.
Each season, the winner of the playoffs is crowned league champion. The CHSL champion compete against Manitoba's other senior league champions for the Manitoba Senior 'A' Provincial Championship.
