| 2021 Co-Champs
2018 & 2019 Co-Champs |
Terryville Black Sox – Milford Hunters
Terryville Black Sox – Blasius Chevrolet |
| 2017 | Watertown Blaze |
| 2016 | Watertown Blaze Naugatuck Dogs (runner-up) |
| 2015 | Naugatuck Dogs Tri-Town Trojans (runner-up) |
| 2014 | Tri-Town Trojans |
| 2013 | Tri-Town Trojans Naugatuck Dogs (runner-up) |
| 2012 | Naugatuck Dogs |
| 2011 | Naugatuck Dogs |
| 2008 | Brass City Brew (runner-up) |
| 2005 | Tribury Turkey Vultures (runner-up) |
| 2000 | Torrington Rebels |
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