| Division Two | |||
| 09/20/2008 | Slaithwaite Utd | 1 - 1 | Cumberworth |
| 09/27/2008 | Cumberworth | 0 - 1 | Westend |
| 10/04/2008 | Stag FC | 0 - 5 | Cumberworth |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Cumberworth | 2 - 0 | Totley Sports |
| 10/18/2008 | Cumberworth | 1 - 1 | Kirkheaton Rovers |
| 10/25/2008 | Berry Brow Lib | 1 - 2 | Cumberworth |
| 11/01/2008 | Cumberworth | 2 - 0 | Slaithwaite Utd |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/08/2008 | Cumberworth | 0 - 1 | Hemsworth Miners |
| 11/22/2008 | Kirkheaton Rovers | 2 - 1 | Cumberworth |
| 12/06/2008 | Netherton | 2 - 3 | Cumberworth |
| FA Challenge Cup Round Two | |||
| 12/20/2008 | Cumberworth | 1 - 2 | Moldgreen Con |
| 01/03/2009 | Moldgreen | 1 - 2 | Cumberworth |
| 01/17/2009 | Mount | 0 - 2 | Cumberworth |
| Barlow Cup Round Two | |||
| 01/24/2009 | Cumberworth | 2 - 4 | Netherton |
| 01/31/2009 | Scholes | 1 - 0 | Cumberworth |
| 02/21/2009 | Cumberworth | 0 - 0 | Moldgreen |
| 02/28/2009 | Westend | 1 - 3 | Cumberworth |
| 03/07/2009 | Cumberworth | 3 - 1 | Stag FC |
| 03/21/2009 | Cumberworth | 2 - 0 | Mount |
| 03/28/2009 | Honley | 0 - 5 | Cumberworth |
| 04/04/2009 | Cumberworth | 1 - 0 | KKS Ashbrow |
| 04/07/2009 | Cumberworth | 1 - 0 | Lamb Inn FC |
| 04/11/2009 | Cumberworth | 2 - 1 | Scholes |
| 04/18/2009 | KKS Ashbrow | 2 - 3 | Cumberworth |
| 04/21/2009 | Cumberworth | 1 - 0 | Berry Brow Lib |
| 04/25/2009 | Cumberworth | 5 - 2 | Honley |
| 04/28/2009 | Cumberworth | 3 - 3 | Netherton |
| 05/02/2009 | Lamb Inn FC | P - P | Cumberworth |