The inaugural championship was contested between the 1997 CNSL champions St. Catharines and Toronto Olympians with the Wolves securing the title in a penalty shootout.

[9] In 2000, the championship received its first title sponsorship from Primus and witnessed the emergence of the Ottawa Wizards after the league's major expansion run in 2001.

[11] After a series of disputes with the CPSL board of directors, Ottawa withdrew from the playoff competition after securing an undefeated regular season in 2003.

The re-emergence of the White Eagles re-sparked the traditional rivalry between Croatia and Serbia, which caused the 2007 championship final to be divided into two matches to segregate the fans.

As the league expanded beyond the Greater Toronto Area and Ontario border a television agreement was reached with Rogers TV, which granted the company naming rights to the championship.

[17] Meanwhile, another milestone was achieved by Trois-Rivières Attak the farm team to the Montreal Impact as it became the first Quebec club to capture the championship in 2009 after defeating Serbia in a 3-2 penalty shootout.