| Saturday 1st September 1990 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Glossop | 1-1 | Skelmersdale United | |
| Tuesday 4th September 1990 | F.A. Challenge Cup Preliminary Round Replay | ||
|---|---|---|---|
| Skelmersdale United | 0-2 | Glossop | |
| Saturday 15th September 1990 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Maine Road | 1-0 | Glossop | |
| Saturday 6th October 1990 | F.A. Carlsberg Vase Preliminary Round | ||
|---|---|---|---|
| Glossop | 2-1 | Waterloo Dock | |
| Saturday 3rd November 1990 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Glossop | 6-1 | Curzon Ashton | |
| Saturday 24th November 1990 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Glossop | 4-0 | Winterton Rangers | |
| Saturday 15th December 1990 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Glossop | 1-0 | North Ferriby United | |
| Saturday 19th January 1991 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Glossop | 2-2 | Cammell Laird | |
| (After Extra Time, 1-1 after 90 mins) | |||
| Tuesday 22nd January 1991 | F.A. Carlsberg Vase 4th Round Replay | ||
|---|---|---|---|
| Cammell Laird | 2-1 | Glossop | |
