| Year | Regular Season Champions | Manager | Playoff Champions | Manager | Playoffs Runner-Up | Manager |
| 1976 | ||||||
| 1977 | Pimlico Hotel/Hambro Hornets | Elan Merkel | ||||
| 1978 | Pimlico Hotel/Hambro Hornets | Elan Merkel | ||||
| 1979 | Bombers | Marc Appel | ||||
| 1980 | Bombers | Marc Appel | Pimlico Hotel/Hambro Hornets | Elan Merkel | ||
| 1981 | Bombers (34-4) | Marc Appel | Pimlico Hotel / Hornets | Elan Merkel | ||
| 1982 | Bombers (30-8) | Marc Appel | Pimlico Hotel / Hornets | Elan Merkel | ||
| 1983 | Bombers | Marc Appel | Bombers | Marc Appel | Ira Gershman | |
| 1984 | Greenies | Lou Greenfeld | Pimlico Hotel / Hornets | Elan Merkel | ||
| 1985 | Bombers | Marc Appel | ||||
| 1986 | Attman's Deli (24-7) | Paul Bell | Bombers | Robert Dubansky | Fader's Dominicans | Gerald Edelman |
| 1987 | Attman's Deli (25-3) | Paul Bell | Attman's Deli (5-0) | Paul Bell | ||
| 1988 | Attman's Deli (25-7) | Paul Bell | Bombers/Hornets | Marc Appel | Attman's Deli (3-2) | Paul Bell |
| 1989 | Attman's Deli (29-1) | Paul Bell | Summerfield (5-1) | Marc Summerfield | Attman's Deli (4-2) | Paul Bell |
| 1990 | Attman's Deli (26-2) | Paul Bell | Bombers/Hornets (5-1) | Richard Berger | Attman's Deli (3-2) | Paul Bell |
| 1991 | Attman's Deli (24-6) | Paul Bell | Attman's Deli (4-1) | Paul Bell | Kings (4-2) | Mike Herr |
| 1992 | Attman's Deli (26-4) | Paul Bell | Attman's Deli (5-0) | Paul Bell | Palmgard (3-2) | Darrin Davis |
| 1993 | Kings (25-5) | Mike Herr | Kings (5-0) | Mike Herr | Money Mailer/ Quizno's (3-2) | Saul Hyatt |
| 1994 | Attman's Deli (25-3) | Paul Bell | Attman's Deli (5-0) | Paul Bell | Money Mailer/ Quizno's (3-2) | Saul Hyatt |
| 1995 | Palmgard (24-4) | Darrin Davis | Palmgard (5-0) | Darrin Davis | Money Mailer/ Quizno's (3-2) | Saul Hyatt |
| 1996 | Attman's Deli (23-3) | Paul Bell | Kings (5-0) | Mike Herr | Palmgard (3-2) | Darrin Davis |
| 1997 | Attman's Deli (28-4) | Paul Bell | Attman's Deli (4-1) | Paul Bell | Kings (4-2) | Mike Herr |
| 1998 | Havana Club Cannons (23-3) | Gerry Edelman | Attman's Deli (5-1) | Paul Bell | Kings (4-2) | Mike Herr |
| 1999 | Attman's Deli (18-10) | Paul Bell | Havana Club Cannons (5-1) | Gerry Edelman | Attman's Deli (3-2) | Paul Bell |
| 2000 | Attman's Deli (22-4) | Paul Bell | Palmgard (5-1) | Jeff Webster | Havana Club Cannons (3-2) | Gerry Edelman |
| 2001 | Havana Club Cannons (18-8) | Gerry Edelman | Attman's Deli (4-1) | Paul Bell | Gorgeous Watches/Quizno's (4-2) | Andrew Rosenstein |
| 2002 | Palmgard (19-5) | Jeff Webster | Gorgeous Watches/Quizno's (5-0) | Andrew Rosenstein | Jilly's Turtles / Attman's Deli (3-2) | Dave Sandler/Rob Ressin |
| 2003 | Quizno's (16-2) | Andrew Rosenstein | Gorgeous Watches/Quizno's (5-0) | Andrew Rosenstein | Havana Club Cannons (3-2) | Gerry Edelman |
| 2004 | Havana Club Cannons (20-2) | Neal Charkatz | Havana Club Cannons (4-1) | Neal Charkatz | Eastern Savings Bank (4-2) | David Finkelstein |
| 2005 | Havana Club Cannons (19-5) | Neal Charkatz | Kings (5-1) | Mike Herr | Eastern Savings Bank (4-2) | David Finkelstein |
| 2006 | Havana Club Cannons (24-2) | Neal Charkatz | Havana Club Cannons (5-1) | Neal Charkatz | Kings (4-2) | Mike Herr |
| 2007 | Havana Club Cannons (27-1) | Neal Charkatz | Havana Club Cannons (4-1) | Neal Charkatz | DC Dental (4-2) | Dovi Ziffer/ Jon Minkove |
| 2008 | Kings (26-2) | Mike Herr | Havana Club Cannons (5-1) | Neal Charkatz | Kings (4-2) | Mike Herr |
| 2009 | Cannons (17-5) | Jeff Kurland | Cannons (4-1) | Jeff Kurland | Kings (4-2) | Mike Herr |
| 2010 | Kings (22-6) | Mike Herr | Kings (4-1) | Mike Herr | Cannons (4-2) | Jeff Kurland |
| 2011 | Sky & Sky Inc. (17-3) | Brian Mekiliesky | Sky & Sky Inc (5-1) | Brian Mekiliesky | Kings (4-2) | Mike Herr |
| 2012 | Kings (22-4) | Mike Herr | Northwest Corridor (4-1) | Howard Goldberg | Sky & Sky Inc (4-2) | Brian Mekiliesky |
| 2013 | Kings (25-1) | Mike Herr | Sky & Sky Inc (5-1) | Brian Mekiliesky | Kings (4-2) | Mike Herr |
| 2014 | Sky & Sky Inc. (21-7) | Brian Mekiliesky | Kings (5-1) | Mike Herr | Sky & Sky Inc (4-2) | Brian Mekiliesky |
| 2015 | Kings (20-4) | Mike Herr | Kings (5-0) | Mike Herr | Nationwide Bombers (3-2) | David Finkelstein |
| 2016 | Nationwide Bombers (16-4) | David Finkelstein | Nationwide Bombers (5-0) | David Finkelstein | Kings (3-2) | Mike Herr |
| 2017 | Natiowide Bombers (18-2) | David Finkelstein | Nationwide Bombers (4-1) | David Finkelstein | Kings (4-2) | Mike Herr |
| 2018 | Nationwide Bombers (15-1) | David Finkelstein | Nationwide Bombers (5-0) | David Finkelstein | Natty O's (3-2) | Jason Smulson |