| Season |
Winners |
Runner-up |
Result |
| 1985-86 |
Old Esthameians |
|
|
| 1986-87 |
Old Aloysians |
|
|
| 1987-88 |
Old Aloysians |
|
|
| 1988-89 |
Old Stationers |
Old Ignatians |
1-0 |
| 1989-90 |
Old Salesians |
|
|
| 1990-91 |
Norsemen |
|
|
| 1991-92 |
West Wickham |
|
|
| 1992-93 |
National Westminster Bank |
Old Hamptonians |
2-2, 3-0 |
| 1993-94 |
Crouch End Vampires |
|
|
| 1994-95 |
National Westminster Bank |
Civil Service |
3-1 |
| 1995-96 |
Old Actonians Association |
Civil Service |
4-0 |
| 1996-97 |
Civil Service |
Lensbury |
|
| 1997-98 |
Old Aloysians |
Old Finchleians |
2-0 |
| 1998-99 |
Old Finchleians |
Honourable Artillery Company |
4-1 |
| 1999-00 |
U C L Academicals |
Crouch End Vampires |
1-1, 4-2 pens |
| 2000-01 |
U C L Academicals |
Civil Service |
2-1 |
| 2001-02 |
Old Meadonians |
Old Actonians Association |
1-1, 4-2 pens |
| 2002-03 |
Winchmore Hill |
Bromleians Sports |
1-0 |
| 2003-04 |
Old Meadonians |
Nottsborough |
3-0 |
| 2004-05 |
Old Meadonians |
Polytechnic |
3-0 |
| 2005-06 |
Winchmore Hill |
Old Owens |
1-0 |
| 2006-07 |
West Wickham |
Old Hamptonians |
4-0 |
| 2007-08 |
Old Meadonians |
Nottsborough |
2-2, 4-3 pens |
| 2008-09 |
Nottsborough |
Polytechnic |
1-0 |
| 2009-10 |
Winchmore Hill |
Nottsborough |
3-0 |
| 2010-11 |
Old Salesians |
Old Carthusians |
3-2 |
| 2011-12 |
Winchmore Hill |
Civil Service |
1-0 |
| 2012-13 |
Old Minchendenians |
Old Salesians |
3-0 |
| 2013-14 |
Old Wilsonians |
Winchmore Hill |
3-1 |
