| Saturday 26th August 2000 | F.A. Challenge Cup Extra Preliminary Round | ||
|---|---|---|---|
| Guisborough Town | 1-1 | Chadderton | |
| Tuesday 29th August 2000 | F.A. Challenge Cup Extra Preliminary Round Replay | ||
|---|---|---|---|
| Chadderton | 4-1 | Guisborough Town | |
| Saturday 2nd September 2000 | F.A. Challenge Cup Preliminary Round | ||
|---|---|---|---|
| Chadderton | 2-3 | Hebburn Town | |
| Saturday 9th September 2000 | F.A. Carlsberg Vase 1st Qualifying Round | ||
|---|---|---|---|
| Chadderton | 1-3 | Rossendale United | |
