| Saturday 29th August 1987 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Colwyn Bay | 3-0 | Winsford United | |
| Saturday 12th September 1987 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Prescot Cables | 0-1 | Colwyn Bay | |
| Saturday 26th September 1987 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Colwyn Bay | 2-2 | Buxton | |
| Tuesday 29th September 1987 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Buxton | 2-5 | Colwyn Bay | |
| Saturday 3rd October 1987 | F.A. Trophy 1st Qualifying Round | ||
|---|---|---|---|
| Eastwood Town | 4-1 | Colwyn Bay | |
| Saturday 10th October 1987 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Alfreton Town | 1-1 | Colwyn Bay | |
| Tuesday 13th October 1987 | F.A. Challenge Cup 3rd Qualifying Round Replay | ||
|---|---|---|---|
| Colwyn Bay | 1-0 | Alfreton Town | |
| Saturday 24th October 1987 | F.A. Challenge Cup 4th Qualifying Round | ||
|---|---|---|---|
| Colwyn Bay | 2-1 | Tow Law Town | |
