| Saturday 2nd September 1989 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Colwyn Bay | 5-1 | Ilkeston Town | |
| Saturday 16th September 1989 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Colwyn Bay | 4-1 | Morecambe | |
| Saturday 23rd September 1989 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Goole Town | 5-2 | Colwyn Bay | |
| Saturday 30th September 1989 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Colwyn Bay | 2-1 | Maine Road | |
| Saturday 14th October 1989 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Colwyn Bay | 1-1 | Congleton Town | |
| Tuesday 17th October 1989 | F.A. Challenge Cup 3rd Qualifying Round Replay | ||
|---|---|---|---|
| Congleton Town | 4-0 | Colwyn Bay | |
