First Round : 09th October 2023| Ponders End CIU | - | Queens Head |
| Sun & Woolpack | - | Maltsters |
| Nomads | - | Old Anchor |
| Warriors | - | Legionares |
| Albert Tots | - | Rising Sun |
| Legion Returns | - | Ponders End W/Mans Club |
| Wheatsheaf Pirates | - | Con Club Hoops |
| Roman Urn | - | Royal B Legion |
Quarter Finals : 6th November 2023
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Semi-Finals : 19th February 2024
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Final : th 2024
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| 2017/18 | Lincoln Arms |
| 2016/17 | Albert Tots |
| 2015/16 | Lincoln Arms |
| 2014/15 | Tommys Tots |
| 2013/14 | Wheatsheaf Enfield |
| 2012/13 | Lincoln Arms |
| 2011/12 | Victoria |
| 2010/11 | Boundary House |
| 2009/10 | Old Comrades 'A' |
| 2008/09 | Green Dragon W/A 'B' |
| 2007/08 | Green Dragon W/A 'B' |
| 2006/07 | White Lion |
| 2005/06 | Kennedys |
| 2004/05 | Gobblers |
| 2003/04 | E.H.W.M Club |
| 2002/03 | E.H.W.M Club |
| 2001/02 | Jolly Bricklayers |
| 2000/01 | Edmonton Utd Services |
| 1999/00 | Bush Hill Park Cons |
| 1998/99 | Prince Albert |
| 1997/98 | Bush Hill Park Cons |
| 1996/97 | Jolly Bricklayers 'A' |
| 1995/96 | Jolly Bricklayers 'A' |
| 1994/95 | Bush Hill Park Cons |
| 1993/94 | Old Comrades 'A' |
| 1992/93 | Old Comrades 'A' |
| 1991/92 | Barnyard 'A' |
| 1990/91 | Barnyard |
| 1989/90 | Barnyard |
| 1988/89 | the Angel |
| 1987/88 | the Angel |