| Division Three | |||
| 30/08/2000 | Cumberworth | 0 - 1 | KKS Ashbrow |
| 06/09/2000 | Golcar Utd | 4 - 2 | Cumberworth |
| 09/09/2000 | Cumberworth | 4 - 3 | Meltham Athletic |
| 23/09/2000 | Cumberworth | 3 - 3 | Aimbry |
| 30/09/2000 | Flockton FC | 2 - 3 | Cumberworth |
| 07/10/2000 | Cumberworth | 6 - 1 | Lockwood |
| Sheffield Junior Challenge Cup Round Two | |||
| 14/10/2000 | New Mill 94 | 2 - 0 | Cumberworth |
| 21/10/2000 | Cumberworth | 1 - 2 | Golcar Utd |
| 28/10/2000 | Cumberworth | 2 - 2 | Little John |
| FA Challenge Cup Round One | |||
| 18/11/2000 | Shelley | 2 - 1 | Cumberworth |
| 25/11/2000 | Black Star | 0 - 2 | Cumberworth |
| 02/12/2000 | Cumberworth | 0 - 4 | H.V.Academicals |
| Groom Cup Round One | |||
| 09/12/2000 | Woodman | 2 - 1 | Cumberworth |
| 16/12/2000 | Cumberworth | 2 - 2 | Shelley |
| 23/12/2000 | Hade Edge | 3 - 4 | Cumberworth |
| 06/01/2001 | Cumberworth | 2 - 0 | Cartworth Moor |
| 13/01/2001 | KKS Ashbrow | 3 - 2 | Cumberworth |
| 03/02/2001 | Cumberworth | 2 - 0 | Flockton FC |
| 17/02/2001 | Cumberworth | 9 - 0 | Black Star |
| 24/02/2001 | Lockwood | 0 - 2 | Cumberworth |
| 10/03/2001 | Little John | 1 - 2 | Cumberworth |
| 17/03/2001 | Meltham Athletic | 6 - 0 | Cumberworth |
| 31/03/2001 | Cartworth Moor | 2 - 4 | Cumberworth |
| 24/04/2001 | Aimbry | 3 - 1 | Cumberworth |
| 28/04/2001 | H.V.Academicals | 5 - 1 | Cumberworth |
| 01/05/2001 | Weavers | 0 - 0 | Cumberworth |
| 01/05/2001 | Shelley | 0 - 0 | Cumberworth |
| 01/05/2001 | Cumberworth | 0 - 0 | Weavers |
| 01/05/2001 | Cumberworth | 0 - 0 | Hade Edge |