| Division Three | |||
| 03/09/2005 | Cumberworth | 1 - 0 | Fenay Bridge FC |
| 17/09/2005 | Lindley | 3 - 3 | Cumberworth |
| 24/09/2005 | Cumberworth | 0 - 0 | Linthwaite Athletic |
| 01/10/2005 | Scholes | 3 - 0 | Cumberworth |
| Sheffield Junior Challenge Cup Round Two | |||
| 08/10/2005 | Cumberworth | 4 - 0 | Conisborough |
| 15/10/2005 | Cumberworth | 4 - 1 | Scissett |
| 22/10/2005 | Sikh Leisure Centre | 2 - 3 | Cumberworth |
| 29/10/2005 | Cumberworth | 1 - 1 | H.V.Academicals |
| 05/11/2005 | Cartworth Moor | 0 - 5 | Cumberworth |
| Sheffield Junior Challenge Cup Round Three | |||
| 12/11/2005 | Grove Central | 2 - 2 | Cumberworth |
| 26/11/2005 | Cumberworth | 2 - 0 | Berry Brow Lib |
| 03/12/2005 | Cravens | 1 - 2 | Cumberworth |
| Sheffield Junior Challenge Cup Round Four | |||
| 10/12/2005 | Slipper FC | 2 - 4 | Cumberworth |
| Groom Cup Round One | |||
| 07/01/2006 | Ireti Athletic | 1 - 9 | Cumberworth |
| Sheffield Junior Trophy Round Five, Quarter Final | |||
| 14/01/2006 | Tomtreddlehoyle | 3 - 0 | Cumberworth |
| FA Challenge Cup Round Two | |||
| 21/01/2006 | Cumberworth | 0 - 1 | Storthes Hall (WR) |
| 28/01/2006 | Cumberworth | 2 - 0 | Hade Edge |
| 04/02/2006 | Cumberworth | 1 - 0 | Lindley |
| Groom Cup Round Two | |||
| 11/02/2006 | Cumberworth | 2 - 0 | Hade Edge |
| 18/02/2006 | Cumberworth | 1 - 2 | Scholes |
| 25/02/2006 | Berry Brow Lib | 1 - 1 | Cumberworth |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2006 | Cravens | 3 - 2 | Cumberworth |
| 18/03/2006 | Cumberworth | 5 - 0 | Cartworth Moor |
| 25/03/2006 | H.V.Academicals | 3 - 5 | Cumberworth |
| 01/04/2006 | Cumberworth | 1 - 2 | Cravens |
| 06/04/2006 | Space FC | 2 - 2 | Cumberworth |
| 08/04/2006 | Cumberworth | 4 - 0 | Shelley |
| 11/04/2006 | Cumberworth | 2 - 1 | Sikh Leisure Centre |
| 13/04/2006 | Linthwaite Athletic | 2 - 2 | Cumberworth |
| 15/04/2006 | Fenay Bridge FC | 2 - 4 | Cumberworth |
| 18/04/2006 | Shelley | 1 - 2 | Cumberworth |
| 22/04/2006 | Scissett | 2 - 2 | Cumberworth |
| 25/04/2006 | Cumberworth | 1 - 1 | Space FC |
| 29/04/2006 | Hade Edge | 0 - 5 | Cumberworth |