|
| YEAR | CHAMPION | PLAYOFF 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 | John Gregorio (P) |
| 1987 | M & M Club | John Gregorio (P) & John McGrath (P) |
| 1988 | United Cleaners | Jim Burgio (1B) |
| 1989 | Teamsters Pub | |
| 1990 | Ocean Kai | Paul Alessi (P) |
| 1991 | Ocean Kai | Jim Burgio (1B) & Angelo 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 | Dawgs | Jerry Thomes (P) |
| 2009 | Shennanigans | Steve Stalcup (2B) & Luis Colon (SS) |
| 2010 | Shennanigans | team award |
| 2011 | Shennanigans | Sam Acevedo (P) & Mike Hoadley (P) |
| 2012 | Shennanigans | Mike Hoadley (P) |
| 2013 | Shennanigans | Nick French (P) |
| 2014 | "A" Division - Shenannigans
"B" Division - STATS Bar & Grille | "A" (MVP) - Nick French (P)
"B" (MVP) Mark Preziosi (SS) and Jack Atton (P) |
| 2015 | Pirates | Charlie Conners (OF) & Kevin O'Hara (OF) |
| 2016 | Magix Box | Mike Selig (C) & Rocky Pisa (P) |
| 2017 | Southside Tavern | Jason Calnan (P) |
| 2018 | "A" Division - Southside Tavern
"B" Division - City Tap House | "A" (MVP) - team award
"B" (MVP) Chris Boyd (P) |
| 2019 | "A" Division - Pat Simpson Club
"B" Division - Telegraph Hill | "A" (MVP) - Mike Garland (P) and Mike Lush (SS)
"B" (MVP) Mike Araujo (P) |
| 2020 | "A" Division - Lincoln Tavern
"B" Division - DRC | "A" (MVP) - Chris Boyd (P)
"B" (MVP) Jason Maxwell (P) |
| 2021 | "A" Division - Lincoln Tavern
"B" Division - Playwright Shamrocks | "A" (MVP) - Nick French (P)
"B" (MVP) - Sean Higgins (P) |
| 2022 | "A" Division - MJS Construction
"B" Division - Publico | "A" (MVP) - Nick French (P)
"B" (MVP) - Alberto Vasquez (P) |
| 2023 | Lincoln Tavern | Gerry Sarro (P) & Conor Gleason (IF/OF) |
