| 2018 & 2019 Co-Champs | 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 |
2019 Season
| Team | Record | GB |
 | 16-2 | 0 |
 | 16-2 | 0 |
 | 14-4 | 2 |
 | 14-4 | 2 |
 | 10-7 | 5.5 |
 | 9-8 | 6.5 |
 | 9-9 | 7 |
 | 9-9 | 7 |
 | 9-9 | 7 |
 | 8-10 | 8 |
 | 8-10 | 8 |
 | 7-11 | 9 |
 | 6-11 | 9.5 |
 | 6-12 | 10 |
 | 5-13 | 11 |
 | 3-14 | 12.5 |
 | 2-16 | 14 |
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