League History (Regular Season, Tournament, Golden Boot Spring Tournament)
| Year | Regular Season Champions | Tournament Winners | Tournament Runners Up | Golden Boot Winners (Spring) | Fair Play Award |
|---|---|---|---|---|---|
| 2025 | Green | Green | South County | Pittsfield | Williamstown |
| 2024 | Green | Green | South County | South County | |
| 2023 | South County | Green | South County | Lenox | Pittsfield |
| 2022 | Green | Lenox | South County | South County | Pittsfield |
| 2021 | South County | ||||
| 2020 | NA | NA | NA | NA | NA |
| 2019 | South County | Willamstown | South County | Williamstown | |
| 2018 | Pittsfield | Pittsfield | North Adams | Williamstown | |
| 2017 | Pittsfield | South County | Pittsfield | North Adams | |
| 2016 | South County | Pittsfield | North Adams | South County | |
| 2015 | South County | Pittsfield | South County | NA | |
| 2014 | Lenox | South County | Williamstown | Williamstown | |
| 2013 | South County | Pittsfield | Williamstown | South County | |
| 2012 | South County | South County | Pittsfield | Pittsfield | |
| 2011 | South County | South County | Pittsfield | Williamstown | |
| 2010 | Pittsfield | Pittsfield | Lenox | ||
| 2009 | Pittsfield | Pittsfield | Williamstown | ||
| 2008 | Pittsfield | Lenox | Pittsfield | ||
| 2007 | South County | Pittsfield | South County | ||
| 2006 | South County | Pittsfield | NA | ||
| 2005 | Pittsfield | Pittsfield | NA | ||
| 2004 | Pittsfield | Lenox | NA | ||
| 2003 | South County | South County | NA | ||
| 2002 | South County | NA | NA |