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| | Champions |
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| YEAR | LEAGUE CHAMPION | MVP |
| 1970 | Brian Wallace Club | Bob "Chick" Noonan (P) |
| 1971 | I.A. Restaurant | Ed Bonnano (P) |
| 1972 | Pleasure Bay Lounge | Bob "Chick" Noonan (P) |
| 1973 | Pleasure Bay Lounge | Bob "Chick" Noonan (P) |
| 1974 | Chippewas | |
| 1975 | Chippewas | Jim Rooney |
| 1976 | Gavin's
Tavern | Billy Elliot (P) |
| 1977 | Canavan's Pub | Tommy Greene (P) & J.Gorham |
| 1978 | YIP Club | John Evans |
| 1979 | YIP Club | Edso Foley (P) |
| 1980 | Triple O's Lounge | Larry Lucas (P) |
| 1981 | Olde Towne Tavern | Ed Bonnano (P) |
| 1982 | L Street Tavern | Larry Lucas (P) |
| 1983 | L Street Tavern | Larry Lucas (P) |
| 1984 | L Street Tavern | Larry Lucas (P) |
| 1985 | Court's Inn | Joey Ward (OF) |
| 1986 | Boston Teacher's Union | |
| 1987 | | |
| 1988 | United Cleaners | Jim Burgio (1B) |
| 1989 | Teamsters Pub | |
| 1990 | Ocean Kai | Paul Alessi (P) |
| 1991 | Ocean Kai | Jim Burgio (1B) & Angie Lapaglia (OF) |
| 1992 | L Street Tavern | Paul Alessi (P) |
| 1993 | L Street Tavern | Ed Toland (3B) |
| 1994 | L Street Tavern | Paul Alessi (P) |
| 1995 | DJ Linnehan's | Ronny Gurley (SS) |
| 1996 | No Champion | |
| 1997 | Sam Moran Club | Dennis Lynch (2B) |
| 1998 | Sam Moran Club | John Gregorio (P) |
| 1999 | Sam Moran Club | Brendan Flynn (OF) & Joey Magee (2B) |
| 2000 | Sidewalk Cafe | Mark Senna (P) |
| 2001 | Sidewalk Cafe | Mark Senna (P) |
| 2002 | Sidewalk Cafe | George Pratt (P) |
| 2003 | Sidewalk Cafe | Bobby Dobay (OF) & George Pratt (P) |
| 2004 | The Playwright | Jerry Thomes (P) |
| 2005 | The Playwright | Jerry Thomes (P), Domenic Lemarra (P), & Jack Rogers (IF) |
| 2006 | Sidewalk Cafe | Mark Senna (P), Peter John (OF), & Bobby Dobay (C) |
| 2007 | Lynx | Domenic Lemarra (P) & Toco Soto (2B) |
| 2008 | | |
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