| Reserve Division Three | |||
| 09/13/2008 | Meltham Athletic 'A' | 0 - 4 | Cumberworth 'A' |
| 09/20/2008 | Cumberworth 'A' | 3 - 3 | Netherton 'A' |
| 09/27/2008 | Holmbridge Res | 0 - 6 | Cumberworth 'A' |
| 10/04/2008 | Cumberworth 'A' | 3 - 4 | Shelley Res |
| 10/11/2008 | Paddock Rangers Res | 3 - 4 | Cumberworth 'A' |
| 10/18/2008 | Shelley Res | 1 - 0 | Cumberworth 'A' |
| 10/25/2008 | Cumberworth 'A' | 6 - 2 | Cartworth Moor Res |
| 11/01/2008 | KKS Ashbrow Res | 2 - 2 | Cumberworth 'A' |
| 11/08/2008 | Cumberworth 'A' | 4 - 2 | Holmbridge Res |
| 11/22/2008 | Upperthong Res | 3 - 3 | Cumberworth 'A' |
| 11/29/2008 | Cumberworth 'A' | 6 - 2 | Brook Motors Res |
| 12/06/2008 | Honley 'A' | 1 - 5 | Cumberworth 'A' |
| 12/20/2008 | Netherton 'A' | 2 - 4 | Cumberworth 'A' |
| 01/03/2009 | Cumberworth 'A' | 0 - 3 | Meltham Athletic 'A' |
| 01/31/2009 | Cumberworth 'A' | 4 - 3 | Kirkheaton Rovers 'A' |
| 02/21/2009 | Cartworth Moor Res | 3 - 3 | Cumberworth 'A' |
| 03/07/2009 | Cumberworth 'A' | 0 - 1 | Upperthong Res |
| Gee Cup Round Three Quarter Final | |||
| 03/14/2009 | Meltham Athletic 'A' | 3 - 5 | Cumberworth 'A' |
| 03/21/2009 | Cumberworth 'A' | 2 - 3 | KKS Ashbrow Res |
| 03/28/2009 | Brook Motors Res | 2 - 2 | Cumberworth 'A' |
| 04/04/2009 | Cumberworth 'A' | 6 - 3 | Honley 'A' |
| Gee Cup Semi Final | |||
| 04/09/2009 | Lindley AFC Res | 5 - 4 | Cumberworth 'A' |
| 04/11/2009 | Cumberworth 'A' | 1 - 3 | Paddock Rangers Res |
| 05/02/2009 | Kirkheaton Rovers 'A' | 3 - 2 | Cumberworth 'A' |