| Saturday 17th September 1988 | |||
|---|---|---|---|
| F.A. Challenge Cup 1st Qualifying Round | |||
| Colwyn Bay | 0-0 | Ashton United | |
| Tuesday 20th September 1988 | |||
|---|---|---|---|
| F.A. Challenge Cup 1st Qualifying Round Replay | |||
| Ashton United | 2-1 | Colwyn Bay | |
| Saturday 24th September 1988 | |||
|---|---|---|---|
| F.A. Trophy 1st Qualifying Round | |||
| Sutton Coldfield Town | 2-3 | Colwyn Bay | |
| Saturday 22nd October 1988 | |||
|---|---|---|---|
| F.A. Trophy 2nd Qualifying Round | |||
| Colwyn Bay | 2-1 | Hednesford Town | |
| Saturday 3rd December 1988 | |||
|---|---|---|---|
| F.A. Trophy 3rd Qualifying Round | |||
| Corby Town | 2-2 | Colwyn Bay | |
| Tuesday 6th December 1988 | |||
|---|---|---|---|
| F.A. Trophy 3rd Qualifying Round Replay | |||
| Colwyn Bay | 2-1 | Corby Town | |
| Saturday 14th January 1989 | |||
|---|---|---|---|
| F.A. Trophy 1st Round | |||
| Colwyn Bay | 1-1 | Frickley Athletic | |
| Saturday 21st January 1989 | |||
|---|---|---|---|
| F.A. Trophy 1st Round Replay | |||
| Frickley Athletic | 3-0 | Colwyn Bay | |
