| Division Four | |||
| 09/09/2000 | Deanhousemuir | 4 - 4 | Holmbridge |
| Sheffield Junior Challenge Cup Round One | |||
| 23/09/2000 | Holmbridge | 4 - 3 | Higham Miners Fossils |
| 30/09/2000 | Holmbridge | 7 - 2 | The Stag FC |
| 07/10/2000 | Holmbridge | 1 - 0 | Woodman |
| Sheffield Junior Challenge Cup Round Two | |||
| 21/10/2000 | Holmbridge | 2 - 3 | Manor Youth |
| 25/11/2000 | Holmbridge | 2 - 3 | Netherthong |
| 02/12/2000 | Lindley | 3 - 1 | Holmbridge |
| 23/12/2000 | Holmbridge | 4 - 2 | Brook Motors |
| 06/01/2001 | G.P.O. Sports | 1 - 2 | Holmbridge |
| Groom Cup Round One | |||
| 13/01/2001 | Lindley | 1 - 3 | Holmbridge |
| 27/01/2001 | Holmbridge | 2 - 3 | Upperthong SC |
| FA Challenge Cup Round One | |||
| 03/02/2001 | Springhead () | 2 - 3 | Holmbridge |
| FA Challenge Cup Round Two | |||
| 17/02/2001 | Holmbridge | 0 - 2 | Flockton FC |
| 24/02/2001 | Scapegoat Hill Utd | 3 - 1 | Holmbridge |
| Groom Cup Round Two | |||
| 10/03/2001 | Holmbridge | 4 - 3 | KKS Ashbrow |
| 17/03/2001 | Holmbridge | 1 - 2 | Scapegoat Hill Utd |
| Groom Cup Round Three Quarter Final | |||
| 31/03/2001 | Golcar Utd | 2 - 1 | Holmbridge |
| 10/04/2001 | Woodman | 1 - 4 | Holmbridge |
| 12/04/2001 | Holmbridge | 2 - 1 | G.P.O. Sports |
| 14/04/2001 | Upperthong SC | 0 - 3 | Holmbridge |
| 17/04/2001 | Cravens | 0 - 1 | Holmbridge |
| 19/04/2001 | Holmbridge | 2 - 1 | Lindley |
| 21/04/2001 | Holmbridge | 2 - 2 | Deanhousemuir |
| 24/04/2001 | Brook Motors | 1 - 3 | Holmbridge |
| 26/04/2001 | Holmbridge | 4 - 2 | Cravens |
| 28/04/2001 | Moldgreen | 4 - 8 | Holmbridge |
| 01/05/2001 | The Stag FC | 0 - 0 | Holmbridge |
| 01/05/2001 | Holmbridge | 0 - 0 | Moldgreen |
| 01/05/2001 | Netherthong | 0 - 0 | Holmbridge |