| Saturday 19th September 1998 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Bourne Town | 1-2 | Glossop North End | |
| Saturday 3rd October 1998 | F.A. Challenge Cup 2nd Qualifying Round | ||
|---|---|---|---|
| Cambridge City | 1-1 | Glossop North End | |
| Tuesday 6th October 1998 | F.A. Challenge Cup 2nd Qualifying Round Replay | ||
|---|---|---|---|
| Glossop North End | 1-1 | Cambridge City | |
| (After Extra Time, Glossop North End won 5-4 on penalties) | |||
| Saturday 10th October 1998 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Glossop North End | 2-1 | Sandwell Borough | |
| Saturday 17th October 1998 | F.A. Challenge Cup 3rd Qualifying Round | ||
|---|---|---|---|
| Glossop North End | 2-3 | Grantham Town | |
| Saturday 7th November 1998 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Birstall United | 3-0 | Glossop North End | |
