| Division One | |||
| 30/08/2000 | Kirkheaton Rovers | 1 - 3 | Wooldale Wanderers |
| 06/09/2000 | Wooldale Wanderers | 1 - 1 | Brackenhall Utd |
| 09/09/2000 | Wooldale Wanderers | 1 - 1 | Slaithwaite Utd |
| 23/09/2000 | Wooldale Wanderers | 5 - 1 | Skelmanthorpe |
| 30/09/2000 | Sovereign Sports | 2 - 3 | Wooldale Wanderers |
| 07/10/2000 | Shepley | 0 - 5 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Two | |||
| 14/10/2000 | Wooldale Wanderers | 5 - 1 | Cartworth Moor |
| FA Challenge Cup Preliminary Round | |||
| 21/10/2000 | Wooldale Wanderers | 5 - 2 | KKS Ashbrow |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/11/2000 | Grange Moor | 3 - 2 | Wooldale Wanderers |
| FA Challenge Cup Round One | |||
| 18/11/2000 | Wooldale Wanderers | 0 - 1 | Shepley |
| 25/11/2000 | Honley | 2 - 2 | Wooldale Wanderers |
| 16/12/2000 | Britannia Sports | 2 - 2 | Wooldale Wanderers |
| Barlow Cup Round One | |||
| 23/12/2000 | Wooldale Wanderers | 4 - 2 | Brackenhall Utd |
| 06/01/2001 | Brackenhall Utd | 3 - 0 | Wooldale Wanderers |
| 13/01/2001 | Grange Moor | 2 - 2 | Wooldale Wanderers |
| 27/01/2001 | Slaithwaite Utd | 2 - 1 | Wooldale Wanderers |
| 03/02/2001 | Wooldale Wanderers | 3 - 3 | Kirkheaton Rovers |
| 17/02/2001 | Wooldale Wanderers | 2 - 1 | Almondbury Utd |
| 24/02/2001 | Kirkburton | 2 - 3 | Wooldale Wanderers |
| 10/03/2001 | Wooldale Wanderers | 2 - 5 | Shepley |
| Barlow Cup Round Two | |||
| 24/03/2001 | Wooldale Wanderers | 2 - 1 | Grange Moor |
| Barlow Cup Round Three Quarter Final | |||
| 31/03/2001 | Wooldale Wanderers | 3 - 2 | Diggle |
| 12/04/2001 | Wooldale Wanderers | 2 - 0 | Grange Moor |
| 14/04/2001 | Almondbury Utd | 3 - 0 | Wooldale Wanderers |
| Barlow Cup Semi Final | |||
| 16/04/2001 | Wooldale Wanderers | 2 - 0 | Shepley |
| 21/04/2001 | Wooldale Wanderers | 1 - 2 | Kirkburton |
| 24/04/2001 | Wooldale Wanderers | P - P | Sovereign Sports |
| 26/04/2001 | Wooldale Wanderers | 2 - 3 | Honley |
| 28/04/2001 | Skelmanthorpe | 2 - 1 | Wooldale Wanderers |
| 01/05/2001 | Wooldale Wanderers | 0 - 0 | Britannia Sports |
| Barlow Cup Final | |||
| 07/05/2001 | Wooldale Wanderers | P - P | New Mill 94 |