| P.E.W/Man C"A" | 4-8 | Townmead |
Quarter Finals : 15th November 2021
| Queens Head | 6-8 | Legionares |
| Rising Sun | 5-8 | Ches, R.B.Legion |
| Red Cow | 4-8 | Maltsters |
| Legion Returns | 8-3 | Townmead |
Semi-finals : 11th April 2022
| Maltsters | 0-8 | Cheshunt RB Legion |
| Legionares | 8-5 | Legion Returns |
Final : 16th May 2022
| Cheshunt RB Legion | 1-8 | Legionares |
| 2017/18 | Legionnaires |
| 2016/17 | Legionnaires |
| 2015/16 | Old Anchor |
| 2014/15 | E.S & S.C |
| 2013/14 | Roman Urn |
| 2012/13 | Falcon |
| 2011/12 | Green Dragon W/A 'A' |
| 2010/11 | Brimsdown |
| 2009/10 | Comrades 'B' |
| 2008/09 | Jolly Butchers |
| 2007/08 | Old Comrades 'B' |
| 2006/07 | the Angel |
| 2005/06 | the Angel |
| 2004/05 | Kennedys |
| 2003/04 | the Gobblers |
| 2002/03 | Old Comrades 'A' |
| 2001/02 | Edmonton Utd Ser |
| 2000/01 | the Romans |
| 1999/00 | E.H.W.M Club |
| 1998/99 | the Nomads |
| 1997/98 | Rifles |
| 1996/97 | Rose & Crown |
| 1995/96 | Bush Hill Park Cons |
| 1994/95 | Jolly Farmers |
| 1993/94 | Jolly Bricklayers 'A' |
| 1992/93 | Coach & Horses 'A' |
| 1991/92 | Black Horse |
| 1990/91 | B.R.S.A Club |
| 1989/90 | Jolly Farmers |
| 1988/89 | Beehive Nomads |
| 1986/87 | B.R.S.A Club |
| 1986/87 | W Abby Sports Center |
| 1985/86 | the Vine |
| 1984/85 | Old Comrades |
| 1983/84 | Percival Wanderers |