| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Chester-le-Street Town | 1-3 | St Helens Town | |
| Saturday 4th September 1999 | F.A. Challenge Cup 1st Qualifying Round | ||
|---|---|---|---|
| St Helens Town | 1-1 | Pickering Town | |
| Tuesday 7th September 1999 | F.A. Challenge Cup 1st Qualifying Round Replay | ||
|---|---|---|---|
| Pickering Town | 3-2 | St Helens Town | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Selby Town | 4-1 | St Helens Town | |
