| Saturday 21st August 1999 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Bradford Park Avenue | 1-0 | Prescot Cables | |
| Saturday 25th September 1999 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Prescot Cables | 2-1 | West Auckland Town | |
| Saturday 23rd October 1999 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Brandon United | 0-1 | Prescot Cables | |
| Saturday 13th November 1999 | F.A. Carlsberg Vase 2nd Round | ||
|---|---|---|---|
| Prescot Cables | 2-3 | Consett | |
