Year | Winner | Finalist |
| 2025 | Calgary White Sox | Calgary Diamondbacks |
| 2024 | Calgary Diamondbacks | Calgary Dinos |
| 2023 | Calgary Diamondbacks | Calgary Dukes |
| 2022 | Calgary Diamondbacks | Calgary Canadians |
| 2021 | Calgary Diamondbacks | Calgary Canadians |
| 2020 | Calgary Diamondbacks | Calgary White Sox |
| 2019 | Calgary Wolfpack | Calgary Longhorns |
| 2018 | Calgary Diamondbacks | Calgary Wolfpack |
| 2017 | Calgary Cardinals | Calgary Dukes |
| 2016 | Calgary Diamondbacks | Calgary Giants |
| 2015 | Calgary Longhorns | Calgary Wolfpack |
| 2014 | Calgary Wolfpack | Calgary Giants |
| 2013 | Calgary Longhorns | Calgary Wolfpack |
| 2012 | Calgary Guns | Calgary Diamondbacks |
| 2011 | Calgary Wolfpack | Calgary Gamecocks |
| 2010 | Calgary Gamecocks | Calgary Longhorns |
| 2009 | Calgary Gamecocks | Acme Pirates |
| 2008 | Calgary Longhorns | Calgary Dust Devils |
| 2007 | Calgary Longhorns | Acme Pirates |
| 2006 | Calgary Longhorns | Calgary Dust Devils |
| 2005 | Calgary Dust Devils | Calgary Longhorns |
| 2004 | Calgary Longhorns | Calgary Gamecocks |
| 2003 | Calgary Cardinals | Calgary Longhorns |
| 2002 | Calgary Longhorns | Calgary Dust Devils |