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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-Tache Hockey League, included a large number of imported players.
The CSHL's first season was as an outlaw league, without accreditation from Hockey Manitoba. Three teams competed that season, the Mitchell Mohawks, Ste. Anne Aces, and Landmark Dutchmen. Mitchell won the championship.
In its second season, the CSHL was accepted by Hockey Manitoba. The league doubled to six teams, with the Steinbach Huskies, Grunthal Redwings, and St. Adolphe Hawks being accepted. Mitchell once again captured the championship.
Prior to the third season, the HTHL folded, and two teams joined the CSHL: the La Broquerie Habs and St. Malo Warriors. This brought the league total of teams to 8. The La Broquerie Habs defeated the Ste Anne Aces in 4 straight games to claim the League Championship.
In Season 4, the Steinbach Huskies and the Landmark Dutchmen folded, leaving the league with 6 teams yet again. The La Broquerie Habs defeated Ste Anne in 5 games to claim their second straight league title. La Broquerie, Manitoba also has the distinction of claiming the title as Manitoba Senior A provincial champions.
In Season 5 the Steinbach Huskies rejoined the league which will bringing the league total to 6 as Grunthal Folded. This season produced a champion other than the Mohawks or Habs with the Ste Anne Aces defeating the St Malo Warriors in 7 games to become the 2007-2008 Champions.
In season 6 it was the St. Malo Warriors that ended a 21 year cup drought and captured their first Carillon title. The final was a rather quick series as St. Malo won in 5 games, winning the cup at home against the Ste. Anne's Aces. It was a well deserved championship for a team that had been ousted from the playoffs in game 7's the two previous seasons by the cup winners. The 2009 season represents a special year in St. Malo hockey as both the Senior Warriors and the Junior B Warriors of the KJHL captured their respective titles the same year for the first time in the town's history.
The 2009-10 season saw the Steinbach Huskies winning the Manitoba Provincial 'A' Championships against Souris on March 23rd, by a score of 8-7 over two legs. The Huskies followed up their Provincial championship the following day in a game 7 match up against the La Broquerie Habs. Mike Martens, the captain at the time, scored with 3:13 left in the third period to clinch the seventh and deciding game 4-3. 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.
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