| Comp | Season | Date | Home | Score | Away | Scorers | Video | Attendance | Result |
|---|---|---|---|---|---|---|---|---|---|
| D2 | 1992-1993 | 24/04/1993 | Bolton Wanderers | 5-0 | Chester City | Brown P, Patterson, Seagraves, McGinlay, Winstanley | 8,514 | Win | |
| D2 | 1992-1993 | 17/10/1992 | Chester City | 2-2 | Bolton Wanderers | Reeves, McGinlay | 3,394 | Draw | |
| D3 | 1991-1992 | 08/02/1992 | Bolton Wanderers | 0-0 | Chester City | 6,609 | Draw | ||
| D3 | 1991-1992 | 26/10/1991 | Chester City | 0-1 | Bolton Wanderers | Darby | 1,867 | Win | |
| D3 | 1990-1991 | 11/05/1991 | Bolton Wanderers | 1-0 | Chester City | Cunningham | 12,826 | Win | |
| D3 | 1990-1991 | 03/11/1990 | Chester City | 0-2 | Bolton Wanderers | Reeves, Philliskirk | 2,553 | Win | |
| D3 | 1989-1990 | 31/03/1990 | Chester City | 2-0 | Bolton Wanderers | 2,738 | Loss | ||
| D3 | 1989-1990 | 21/10/1989 | Bolton Wanderers | 1-0 | Chester City | Philliskirk | 6,496 | Win | |
| D3 | 1988-1989 | 01/04/1989 | Chester City | 0-0 | Bolton Wanderers | 3,225 | Draw | ||
| D3 | 1988-1989 | 17/12/1988 | Bolton Wanderers | 0-1 | Chester City | 4,318 | Loss | ||
| LC1L2 | 1988-1989 | 07/09/1988 | Chester City | 3-1 | Bolton Wanderers | Cowdrill | 3,784 | Loss | |
| LC1L1 | 1988-1989 | 30/08/1988 | Bolton Wanderers | 1-0 | Chester City | Darby | 3,535 | Win | |
| D3 | 1986-1987 | 07/03/1987 | Chester City | 0-0 | Bolton Wanderers | 2,764 | Draw | ||
| AMCNQF | 1986-1987 | 10/02/1987 | Bolton Wanderers | 1-2 | Chester City | Came | 3,900 | Loss | |
| D3 | 1986-1987 | 25/10/1986 | Bolton Wanderers | 1-1 | Chester City | Elliott S | 4,607 | Draw | |
| LC1L2 | 1983-1984 | 14/09/1983 | Chester City | 3-0 | Bolton Wanderers | (aet) (Lost 2-0 on penalties) | 1,502 | Loss | |
| LC1L1 | 1983-1984 | 30/08/1983 | Bolton Wanderers | 3-0 | Chester City | Joyce W G, Caldwell 2 | 2,665 | Win |