| Major Division | |
| Season | Team | Manager |
| 2024 | Lynch's Towing | Aaron Monteiro |
| 2023 | Paramount Rug | David Burnham |
| 2022 | | |
| 2021 | Tinrays Family Restaurant | Chris Kelly |
| 2020 | Everetts Auto Parts | Marty Burgess |
| 2019 | Tinrays Family Restaurant | Chris Kelley |
| 2018 | Everetts Auto Parts | Marty Burgess |
| 2017 | Woodwards Auto Parts | John Stevens |
| 2016 | Allied Home Improvement | Steve Hanson & Dan Richarson |
| 2015 | Triple M Movers | Tony Felder |
| 2014 | Woodwards Auto Parts | John Stevens |
| | |
| Minor Division | |
| Season | Team | Manager |
| 2023 | Altitude | Jerron Gerald |
| 2022 | Altitude | Jerron Gerald and Bobby Fortes |
| 2021 | Team Jeffrey Thompson | Steve Clarke |
| 2020 | Brockton North LL | |
| 2019 | Team Mayor Carpenter | John Zonak |
| 2018 | Rockmeadow Realty | Kevin Borges |
| 2017 | HarborOne Bank | John Zonak |
| 2016 | HarborOne Bank | Josh Phillion |
| 2015 | Hanson Plumbing | Chris Kelley |
| 2014 | Churchill Linen | Paul Faria |
| 2013 | Tri Town Associates | Kevin Borges |
| 2012 | Triple M Movers | Tony Felder |
| | |
| Fall Ball |
|
| Season | Team | Manager |
| 2024 | Dodgers | David Burnham |
| 2023 | Red Sox | Joe Labossiere |
| 2022 | | |
| 2021 | Dodgers | Damien Bailey |
| 2020 | Red Sox | Marty Burgess |
| 2019 | Dodgers | Donny Packard |
| 2018 | Dodgers | Donny Packard |
| 2017 | Dodgers | Donny Packard |
| 2016 | Giants | Marty Burgess |
| 2015 | Red Sox | John Stevens |
| 2014 | Orioles | Marty Burgess |
| 2013 | Orioles | Marty Burgess |
| 2012 | Athletics | Arnie Benjamin |