| Division Four | |||
| 09/09/2000 | Upperthong SC | 2 - 8 | Woodman |
| 23/09/2000 | The Stag FC | 2 - 5 | Woodman |
| 30/09/2000 | Woodman | 3 - 2 | Lindley |
| 07/10/2000 | Holmbridge | 1 - 0 | Woodman |
| FA Challenge Cup Round One | |||
| 21/10/2000 | Cravens | 2 - 4 | Woodman |
| 28/10/2000 | Moldgreen | 4 - 1 | Woodman |
| FA Challenge Cup Round Two | |||
| 18/11/2000 | Old Collegians (OBL) | 2 - 1 | Woodman |
| 25/11/2000 | Woodman | 1 - 7 | Scapegoat Hill Utd |
| Groom Cup Round One | |||
| 09/12/2000 | Woodman | 2 - 1 | Cumberworth |
| 23/12/2000 | Woodman | 0 - 4 | Netherthong |
| 06/01/2001 | Netherthong | P - P | Woodman |
| 13/01/2001 | Woodman | 1 - 8 | Deanhousemuir |
| 20/01/2001 | Cravens | 4 - 1 | Woodman |
| 27/01/2001 | Woodman | 6 - 1 | G.P.O. Sports |
| 03/02/2001 | Lindley | 6 - 2 | Woodman |
| 17/02/2001 | Brook Motors | 5 - 1 | Woodman |
| 24/02/2001 | Woodman | 2 - 0 | The Stag FC |
| Groom Cup Round Two | |||
| 10/03/2001 | Scapegoat Hill Utd | 6 - 1 | Woodman |
| 17/03/2001 | Deanhousemuir | 3 - 3 | Woodman |
| 17/03/2001 | G.P.O. Sports | P - P | Woodman |
| 24/03/2001 | Woodman | 0 - 3 | Moldgreen |
| 31/03/2001 | Woodman | P - P | Cravens |
| 10/04/2001 | Woodman | 1 - 4 | Holmbridge |
| 14/04/2001 | Woodman | 3 - 2 | Brook Motors |
| 28/04/2001 | Woodman | 3 - 0 | Upperthong SC |
| 01/05/2001 | Scapegoat Hill Utd | 0 - 0 | Woodman |