| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Stafford Rangers | 2-0 | Glossop North End | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Blackstones | 0-2 | Glossop North End | |
| Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Glossop North End | 4-2 | Bolehall Swifts | |
| Saturday 13th November 1999 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Malvern Town | 2-2 | Glossop North End | |
| (After Extra Time, 2-2 after 90 mins) | |||
| Tuesday 16th November 1999 | F.A. Carlsberg Vase | ||
|---|---|---|---|
| Glossop North End | 3-0 | Malvern Town | |
| Saturday 4th December 1999 | F.A. Carlsberg Vase 3rd Round | ||
|---|---|---|---|
| Glossop North End | 3-2 | Brigg Town | |
| Saturday 22nd January 2000 | F.A. Carlsberg Vase 4th Round | ||
|---|---|---|---|
| Glossop North End | 0-1 | Chippenham Town | |
| (After Extra Time, 0-0 after 90 mins) | |||
