| Saturday 2nd September 2000 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Cheadle Town | 0-1 | Bridlington Town | |
| Saturday 23rd September 2000 | F.A. Carlsberg Vase 2nd Qualifying Round | ||
|---|---|---|---|
| Poulton Victoria | 1-2 | Cheadle Town | |
| Saturday 21st October 2000 | F.A. Carlsberg Vase 1st Round | ||
|---|---|---|---|
| Fleetwood Freeport | 2-0 | Cheadle Town | |
