The Middlesex League was created in 1947-48 and replaced the two inter-club competitions that had been running previously, County Cup (1907-1947) and County Trophy (1912-47).
1947/48 Ealing
1948/49 Ealing
1949/50 Ealing
1950/51 Ealing
1951/52 Harrow
1952/53 Willesden
1953/54 Harrow
1954/55 Harrow
1955/56 Athenaeum
1956/57 William Ellis School
1957/58 Harrow
1958/59 Cedars
1959/60 Harrow
1960/61 Metropolitan
1961/62 Cedars
1962/63 Cedars
1963/64 Islington
1964/65 Islington
1965/66 Metropolitan
1966/67 Islington
1967/68 Islington
1968/69 Athenaeum
1969/70 Harrow
1970/71 Central YMCA
1971/72 Central YMCA
1972/73 Athenaeum
1973/74 Central YMCA
1974/75 Harrow
1975/76 Central YMCA
1976/77 Harrow
1977/78 Harrow
1978/79 Central YMCA
1979/80 Wood Green
1980/81 Wood Green
1981/82 Wood Green
1982/83 Wood Green
1983/84 Wood Green
1984/85 Kings Head
1985/86 Kings Head
1986/87 Hackney
1987/88 Hackney
1988/89 Kings Head
1989/90 Hackney
1990/91 Hampstead
1991/92 Kings Head
1992/93 Kings Head
1993/94 Hampstead
1994/95 West London
1995/96 Imperial College
1996/97 Imperial College
1997/98 Imperial College
1998/99 Imperial College
1999/00 Kings Head
2000/01 Hackney
2001/02 Hackney
2002/03 Athenaeum
2003/04 Kings Head
2004/05 Athenaeum
2005/06 Kings Head
2006/07 Kings Head
2007/08 Kings Head
2008/09 Ealing
2009/10 Hendon
2010/11 Ealing
2011/12 Hendon
2012/13 Hendon
2013/14 Hendon
2014/15 Hendon
2015/16 Hendon
2016/17 Hendon
2017/18 Hendon
2018/19 Hackney
2019/20 Hendon
2020/21 No competition
2021/22 Muswell Hill
2022/23 Hackney