| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Woodley Sports | 2-1 | Ossett Albion | |
| Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| Liversedge | 3-2 | Woodley Sports | |
| Saturday 11th September 1999 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Woodley Sports | 0-3 | Billingham Synthonia | |
