The Chester Cup Winners
| season |
winner |
venue |
opponent |
| 1991 | Northern | (a) | Neston |
| 1992 | Neston | (a) | Northern |
| 1993 | Northern | (h) | Chester Boughton Hall |
| 1994 | Southport and Birkdale | (h) | Formby |
| 1995 | Birkenhead Park | (a) | Bootle |
| 1996 | Bootle | (h) | Neston |
| 1997 | Chester Boughton Hall | (a) | Neston |
| 1998 | Newton le Willows | (a) | Southport and Birkdale |
| 1999 | Bootle | (h) | Southport and Birkdale |
| 2000 | Liverpool | (h) | Huyton |
| 2001 | Ormskirk | (a) | New Brighton |
| 2002 | Newton le Willows | (a) | Highfield |
| 2003 | Ormskirk | (h) | Formby |
| 2004 | Wallasey | (h) | New Brighton |
| 2005 | Bootle | (h) | Formby |
| 2006 | Southport and Birkdale | (a) | Newton le Willows |
| 2007 | Leigh | (h) | Sefton Park |
| 2008 | New Brighton | (a) | Wigan |