| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Bacup Borough | 2-2 | Sheffield | |
| Tuesday 24th August 1999 | F.A. Challenge Cup Preliminary Round Replay | ||
|---|---|---|---|
| Sheffield | 4-0 | Bacup Borough | |
| Saturday 11th September 1999 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Denaby United | 1-0 | Bacup Borough | |
