| Reserve Division One | |||
| 30/08/2000 | Wooldale Wanderers Res | 0 - 7 | Brackenhall Utd Res |
| 06/09/2000 | Heywood Sports Res | 3 - 3 | Wooldale Wanderers Res |
| 09/09/2000 | Shepley Res | 6 - 0 | Wooldale Wanderers Res |
| 23/09/2000 | Honley Res | 8 - 1 | Wooldale Wanderers Res |
| 30/09/2000 | Wooldale Wanderers Res | P - P | Slaithwaite Utd Res |
| 07/10/2000 | Wooldale Wanderers Res | 0 - 5 | Skelmanthorpe Res |
| 21/10/2000 | Kirkheaton Rovers Res | 4 - 1 | Wooldale Wanderers Res |
| 28/10/2000 | Britannia Sports Res | 0 - 5 | Wooldale Wanderers Res |
| 18/11/2000 | Skelmanthorpe Res | P - P | Wooldale Wanderers Res |
| 02/12/2000 | Wooldale Wanderers Res | 4 - 1 | Kirkburton Res |
| 16/12/2000 | Wooldale Wanderers Res | 2 - 4 | Diggle Res |
| 23/12/2000 | Uppermill Res | 5 - 0 | Wooldale Wanderers Res |
| 06/01/2001 | Wooldale Wanderers Res | 2 - 5 | Heywood Sports Res |
| 27/01/2001 | Wooldale Wanderers Res | P - P | Shepley Res |
| Richardson Cup Round One | |||
| 10/02/2001 | Wooldale Wanderers Res | 0 - 2 | Brackenhall Utd Res |
| 17/02/2001 | New Mill 94 Res | 1 - 0 | Wooldale Wanderers Res |
| 24/02/2001 | Wooldale Wanderers Res | 1 - 6 | Kirkheaton Rovers Res |
| Richardson Cup Round One | |||
| 17/03/2001 | Wooldale Wanderers Res | 6 - 3 | Brackenhall Utd Res |
| Richardson Cup Round Two | |||
| 24/03/2001 | Shelley | P - P | Wooldale Wanderers Res |
| Richardson Cup Round Three Quarter Final | |||
| 10/04/2001 | Honley Res | 3 - 4 | Wooldale Wanderers Res |
| Richardson Cup Semi Final | |||
| 12/04/2001 | Uppermill 'A' | 1 - 1 | Wooldale Wanderers Res |
| 14/04/2001 | Wooldale Wanderers Res | 3 - 2 | Uppermill Res |
| Richardson Cup Semi Final | |||
| 17/04/2001 | Uppermill 'A' | 2 - 1 | Wooldale Wanderers Res |
| 19/04/2001 | Brackenhall Utd Res | 5 - 1 | Wooldale Wanderers Res |
| 28/04/2001 | Wooldale Wanderers Res | 7 - 3 | Almondbury Utd Res |
| 01/05/2001 | Wooldale Wanderers Res | 0 - 0 | Honley Res |
| 01/05/2001 | Slaithwaite Utd Res | 0 - 0 | Wooldale Wanderers Res |
| 01/05/2001 | Almondbury Utd Res | 0 - 0 | Wooldale Wanderers Res |
| 01/05/2001 | Wooldale Wanderers Res | 0 - 0 | Britannia Sports Res |
| 01/05/2001 | Diggle Res | 4 - 0 | Wooldale Wanderers Res |
| 01/05/2001 | Wooldale Wanderers Res | 0 - 0 | New Mill 94 Res |
| 01/05/2001 | Kirkburton Res | 0 - 0 | Wooldale Wanderers Res |