| Division Four | |||
| 09/13/2008 | Hade Edge | 5 - 3 | Fenay Bridge FC |
| 09/20/2008 | Marsden | 2 - 3 | Hade Edge |
| 09/27/2008 | Hade Edge | 0 - 1 | Flockton FC |
| 10/04/2008 | Hade Edge | 4 - 2 | Dewsbury Town OB |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Hade Edge | 0 - 5 | Edlington Town FC |
| 10/18/2008 | Farnley Terriers | 5 - 2 | Hade Edge |
| 10/25/2008 | Hade Edge | 3 - 1 | Coach and Horses |
| 11/01/2008 | Dewsbury Town OB | 3 - 2 | Hade Edge |
| 11/08/2008 | Fenay Bridge FC | 4 - 3 | Hade Edge |
| 11/15/2008 | Hade Edge | 2 - 3 | Cartworth Moor |
| 12/06/2008 | Cartworth Moor | 5 - 4 | Hade Edge |
| 12/20/2008 | Hade Edge | 0 - 1 | Marsden |
| 01/03/2009 | Flockton FC | 3 - 1 | Hade Edge |
| 01/24/2009 | Hade Edge | 0 - 6 | Royal Dolphins |
| 01/31/2009 | Hade Edge | 0 - 5 | Farnley Terriers |
| 03/07/2009 | Coach and Horses | 6 - 3 | Hade Edge |
| Groom Cup Round Two | |||
| 03/14/2009 | Holmbridge | 1 - 2 | Hade Edge |
| 03/21/2009 | Royal Dolphins | 4 - 0 | Hade Edge |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Grange Moor | 3 - 1 | Hade Edge |