| Division Three | |||
| 08/09/2007 | Cumberworth | 2 - 2 | Lamb Inn FC |
| 15/09/2007 | H.V.Academicals | 2 - 4 | Cumberworth |
| 22/09/2007 | Cumberworth | 1 - 1 | Heyside FC |
| 29/09/2007 | The Stag FC | 1 - 5 | Cumberworth |
| 06/10/2007 | Lindley | 0 - 7 | Cumberworth |
| Sheffield Junior Challenge Cup Round One | |||
| 13/10/2007 | Aston FC | 2 - 0 | Cumberworth |
| FA Challenge Cup Round One | |||
| 20/10/2007 | Britannia Sports | 3 - 2 | Cumberworth |
| 27/10/2007 | SC Cowlersley | 0 - 3 | Cumberworth |
| 03/11/2007 | Cumberworth | 6 - 0 | Linthwaite Athletic |
| Groom Cup Round One | |||
| 10/11/2007 | Lindley | 4 - 7 | Cumberworth |
| 17/11/2007 | Cumberworth | 0 - 0 | SC Cowlersley |
| 24/11/2007 | Holmbridge | 2 - 2 | Cumberworth |
| 01/12/2007 | Cumberworth | 1 - 1 | Lindley |
| 08/12/2007 | Cumberworth | 4 - 1 | H.V.Academicals |
| 22/12/2007 | Skelmanthorpe | 4 - 2 | Cumberworth |
| 29/12/2007 | Cumberworth | 4 - 2 | Paddock Rangers |
| 05/01/2008 | Upperthong | 0 - 2 | Cumberworth |
| 12/01/2008 | Coach and Horses | 0 - 5 | Cumberworth |
| 16/02/2008 | Cumberworth | 1 - 0 | Grange Moor |
| 23/02/2008 | Lamb Inn FC | 0 - 0 | Cumberworth |
| Groom Cup Round Two | |||
| 08/03/2008 | Y.M.C.A | 0 - 2 | Cumberworth |
| 22/03/2008 | Cumberworth | 1 - 0 | Holmbridge |
| Groom Cup Round Three Quarter Final | |||
| 29/03/2008 | Cumberworth | 4 - 2 | Paddock Rangers |
| 05/04/2008 | Grange Moor | 0 - 3 | Cumberworth |
| 10/04/2008 | Heyside FC | 1 - 1 | Cumberworth |
| 12/04/2008 | Paddock Rangers | 1 - 6 | Cumberworth |
| Groom Cup Semi Final | |||
| 15/04/2008 | Cumberworth | 4 - 2 | The Stag FC |
| 19/04/2008 | Cumberworth | 3 - 0 | Upperthong |
| 26/04/2008 | Cumberworth | 2 - 0 | Skelmanthorpe |
| Groom Cup Final | |||
| 01/05/2008 | Lamb Inn FC | 3 - 0 | Cumberworth |
| 03/05/2008 | Cumberworth | 2 - 0 | Coach and Horses |
| 06/05/2008 | Linthwaite Athletic | 0 - 3 | Cumberworth |
| 10/05/2008 | Cumberworth | 1 - 0 | The Stag FC |