The Chester Cup Winners
.
  season

  winner

venue

 opponent

1 1991  Northern (a)  Neston
2 1992  Neston (a)  Northern
3 1993  Northern (h)  Chester Boughton Hall
4 1994  Southport and Birkdale (h)  Formby
5 1995  Birkenhead Park (a)  Bootle
6 1996  Bootle (h)  Neston
7 1997  Chester Boughton Hall (a)  Neston
8 1998  Newton le Willows (a)  Southport and Birkdale
9 1999  Bootle (h)  Southport and Birkdale
10 2000  Liverpool (h)  Huyton
11 2001  Ormskirk (a)  New Brighton
12 2002  Newton le Willows (a)  Highfield
13 2003  Ormskirk (h)  Formby
14 2004  Wallasey (h)  New Brighton
15 2005  Bootle (h)  Formby
16 2006  Southport and Birkdale (a)  Newton le Willows
17 2007  Leigh (h)  Sefton Park
18 2008  New Brighton (a)  Wigan
19 2009  Bootle (a)  Northop Hall
20 2010  Lytham (a)  Sefton Park
21 2011  New Brighton (a)  Leigh
22 2012  Bootle (a)  Sefton Park
23 2013  New Brighton (h)  Northern
24 2014  Wallasey (h)  Birkenhead Park
25 2015  Ormskirk (a)  Bootle
26 2016  Northern (a)  Ormskirk
27 2017  Northern (h)  Ormskirk
. .
 wins in finals:  defeats in finals:
. .
 5  3
 Bootle  Formby
 4  Neston
 Northern  Sefton Park
 3  2
 New Brighton  Bootle
 Ormskirk  New Brighton
 2  Northern
 Newton le Willows  Ormskirk
 Southport and Birkdale  Southport and Birkdale
 Wallasey  1
 1  Birkenhead Park
 Birkenhead Park  Chester Boughton Hall
 Chester Boughton Hall  Highfield
 Leigh  Huyton
 Liverpool  Leigh
 Lytham  Newton le Willows
 Neston  Northop Hall
.  .  Wigan
. .12 wins by home team  .

 15 wins by away team

 ..