| Division Four | |||
| 09/09/2000 | Deanhousemuir | 4 - 4 | Holmbridge |
| 23/09/2000 | Deanhousemuir | 3 - 2 | Scapegoat Hill Utd |
| 30/09/2000 | Cravens | 4 - 5 | Deanhousemuir |
| 07/10/2000 | Deanhousemuir | 2 - 0 | Netherthong |
| Sheffield Junior Challenge Cup Round Two | |||
| 21/10/2000 | Deanhousemuir | 2 - 3 | New Lodge WMC |
| 28/10/2000 | Deanhousemuir | 5 - 4 | Brook Motors |
| FA Challenge Cup Round One | |||
| 18/11/2000 | Deanhousemuir | 2 - 0 | Woolpack St John |
| 25/11/2000 | G.P.O. Sports | 1 - 1 | Deanhousemuir |
| 02/12/2000 | Deanhousemuir | 3 - 3 | Upperthong SC |
| Groom Cup Round One | |||
| 09/12/2000 | Lockwood | P - P | Deanhousemuir |
| FA Challenge Cup Round Two | |||
| 16/12/2000 | Almondburians (OBL) | 5 - 1 | Deanhousemuir |
| 23/12/2000 | The Stag FC | 1 - 1 | Deanhousemuir |
| 06/01/2001 | Deanhousemuir | 1 - 5 | Moldgreen |
| 13/01/2001 | Woodman | 1 - 8 | Deanhousemuir |
| 20/01/2001 | Deanhousemuir | 10 - 1 | G.P.O. Sports |
| 27/01/2001 | Scapegoat Hill Utd | 2 - 1 | Deanhousemuir |
| 03/02/2001 | Deanhousemuir | 3 - 1 | The Stag FC |
| 17/02/2001 | Upperthong SC | 1 - 2 | Deanhousemuir |
| 24/02/2001 | Brook Motors | 2 - 4 | Deanhousemuir |
| 10/03/2001 | Moldgreen | 4 - 2 | Deanhousemuir |
| 17/03/2001 | Deanhousemuir | 3 - 3 | Woodman |
| 24/03/2001 | Lindley | 5 - 6 | Deanhousemuir |
| 31/03/2001 | Netherthong | 4 - 4 | Deanhousemuir |
| 07/04/2001 | Deanhousemuir | P - P | Lindley |
| 14/04/2001 | Deanhousemuir | 1 - 4 | Cravens |
| 21/04/2001 | Holmbridge | 2 - 2 | Deanhousemuir |