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The 1999 Canadian Professional Soccer League season was the second season under the Canadian Professional Soccer League name. The season began on May 28, 1999, and concluded on October 2, 1999, with Toronto Olympians defeating Toronto Croatia 2-0 to claim their first CPSL Championship. The Olympians made history by becoming the first club in the league's history to achieve a treble. For the second straight season, they went undefeated for the entire season. The league also introduced their first All-Star match where the CPSL All-Stars faced the CSA Development team.
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