INTERCITY LEAGUE PLAYOFF CHAMPIONS FROM 1960-2024
| Year | Champions | Runner-up |
| 2025 | Lexington Blue Sox | Lexington Bull Dogs |
| 2024 | Andre Chiefs | Lexington Blue Sox |
| 2023 | Andre Chiefs | Sabertooth Expos |
| 2022 | Middlesex Expos | Lexington Blue Sox |
| 2021 | Lexington Blue Sox | Middlesex Expos |
| 2020 | Season Canceled | Due to COVID |
| 2019 | Lexington Blue Sox | Alibrandis |
| 2018 | Lexington Blue Sox | Watertown |
| 2017 | Lexington Blue Sox | Reading Bulldogs |
| 2016 | Lexington Blue Sox | Andre Chiefs |
| 2015 | Lexington Blue Sox | Andre Chiefs |
| 2014 | Andre Chiefs | Lexington Blue Sox |
| 2013 | Lexington Blue Sox | Andre Chiefs |
| 2012 | Andre Chiefs | Lexington Blue Sox |
| 2011 | Lexington Blue Sox | Andre Chiefs |
| 2010 | Lexington Blue Sox | Watertown Reds |
| 2009 | Lexington Blue Sox | Andre Chiefs |
| 2008 | Lexington Blue Sox | Cassell Club |
| 2007 | Lexington Blue Sox | Cassell Club |
| 2006 | Cassell Club | Watertown Reds |
| 2005 | Lexington Blue Sox | Cassell Club |
| 2004 | Lexington Blue Sox | Lowell Braves |
| 2003 | Gately Rams | Lexington Blue Sox |
| 2002 | Lexington Blue Sox | Gately Rams |
| 2001 | Gately Rams | Andre Chiefs |
| 2000 | Lowell Braves | Gately Rams |
| 1999 | Anthony’s A’s | Lowell Braves |
| 1998 | Lexington Blue Sox | Cremones A’s |
| 1997 | Andre Chiefs | Wilmington |
| 1996 | Holovak & Coughlin | Cremones A’s |
| 1995 | Andre Chiefs | Martini Woburn |
| 1994 | Wakefield Merchants | Augustine’s A’s |
| 1993 | Melrose Rams | Andre Chiefs |
| 1992 | Andre Chiefs | Augustine’s A’s |
| 1991 | Melrose Rams | Andre Chiefs |
| 1990 | Andre Chiefs | Augustine’s A’s |
| 1989 | Melrose Rams | Wakefield Merchants |
| 1988 | Melrose Rams | Wakefield Merchants |
| 1987 | Melrose Rams | Medford Mustangs |
| 1986 | Melrose Rams | Grannan Club |
| 1985 | Medford Mustangs | Melrose Rams |
| 1984 | Augustine’s A’s | Wakefield Merchants |
| 1983 | Augustine’s A’s | Somerville Elms |
| 1982 | Augustine’s A’s | Somerville Elms |
| 1981 | Augustine’s A’s | Hosmer Chiefs |
| 1980 | Hosmer Chiefs | Arlex Oilers |
| 1979 | Hosmer Chiefs | Augustine’s A’s |
| 1978 | Wakefield Merchants | Augustine’s A’s |
| 1977 | Augustine’s A’s | Waltham |
| 1976 | Augustine’s A’s | Hosmer Chiefs |
| 1975 | Augustine’s A’s | Hosmer Chiefs |
| 1974 | Hosmer Chiefs | Malden City Club |
| 1973 | Hosmer Chiefs | Wakefield Merchants |
| 1972 | Malden City Club | Wakefield Merchants |
| 1971 | Hosmer Chiefs | Wakefield Merchants |
| 1970 | Hosmer Chiefs | Boston Typos |
| 1969 | Hosmer Chiefs | Wakefield Merchants |
| 1968 | Hosmer Chiefs | Wakefield Merchants |
| 1967 | Reading | Wilmington |
| 1966 | Wilmington | Reading |
| 1965 | North Cambridge | Reading |
| 1964 | Winchester | North Cambridge |
| 1963 | North Cambridge | Wakefield Merchants |
| 1962 | North Cambridge | Winchester |
| 1961 | North Cambridge | Reading |
| 1960 | North Cambridge | Reading |