Past Champions
| Season |
YBL champion |
YBL runner-up |
Result |
| 2024 |
Brighton Black Sox |
Brighton Braves |
4-3 |
| 2023 |
Brighton Black Sox |
Al Thomas Athletics |
4-1 |
| 2022 |
Al Thomas Athletics |
Brighton Black Sox |
4-1 |
| 2021 |
Al Thomas Athletics |
Brighton Black Sox |
4-0 |
| 2020 |
East Boston Expos |
Charlestown Townies |
3-2 |
| 2019 |
Revere Rockies |
Charlestown Townies |
4-2 |
| 2018 |
Brighton Braves |
Revere Rockies |
4-3 |
| 2017 |
Alibrandis Baseball |
Brighton Braves |
4-3 |
| 2016 |
Somerville Alibrandis |
Al Thomas Athletics |
4-0 |
| 2015 |
Somerville Alibrandis |
East Boston Knights |
4-0 |
| 2014 |
Somerville Alibrandis |
AlThomas Athletics |
4-1 |
| 2013 |
Somerville Alibrandis |
Revere Rockies |
4-0 |
| 2012 |
Somerville Alibrandis |
Malden Bulldogs |
4-1 |
| 2011 |
Somerville Alibrandis |
Malden Bulldogs |
4-1 |
| 2010 |
Somerville Alibrandis |
Bluefish Baseball Club |
4-1 |
| 2009 |
Bluefish Baseball Club |
Malden Bulldogs |
4-0 |
| 2008 |
Bluefish Baseball Club |
Brighton Brewers |
4-1 |
| 2007 |
Somerville Alibrandis |
Brighton Brewers |
4-1 |
| 2006 |
Somerville Alibrandis |
Medford Maddogs |
4-1 |
| 2005 |
Somerville Alibrandis |
Al Thomas Athletics |
4-3 |
| 2004 |
Somerville Alibrandis |
South Boston Saints |
4-1 |
| 2003 |
Somerville Alibrandis |
East Boston Blue Sox |
4-0 |
| 2002 |
Somerville Alibrandis |
South Boston Saints |
4-0 |
| 2001 |
Somerville Alibrandis |
Brighton Black Sox |
4-1 |
| 2000 |
Somerville Alibrandis |
McKay Club Beacons |
4-1 |
| 1999 |
Somerville Alibrandis |
South Boston Saints |
4-0 |
| 1998 |
Cambridge Bucs |
McKay Club Beacons |
4-2 |
| 1997 |
Somerville Alibrandis |
Brighton Lincoln Sox |
4-3 |
| 1996 |
Brighton Lincoln Sox |
Al Thomas Athletics |
4-0 |
| 1995 |
Brighton Lincoln Sox |
Al Thomas Athletics |
4-3 |
| 1994 |
Boston Padres |
Al Thomas Athletics |
4-2 |
| 1993 |
Al Thomas Athletics |
Savin Hill Hornets |
4-3 |
| 1992 |
East Boston |
McKay Club |
4-1 |
| 1991 |
Brighton Dodgers |
East Boston |
4-2 |
| 1990 |
Al Thomas Athletics |
East Boston |
4-? |