| Division Four | |||
| 09/13/2008 | Hade Edge | 5 - 3 | Fenay Bridge FC |
| 09/20/2008 | Fenay Bridge FC | 1 - 0 | Cartworth Moor |
| 09/27/2008 | Coach and Horses | 2 - 3 | Fenay Bridge FC |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Moldgreen | 7 - 1 | Fenay Bridge FC |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Grange Moor | 4 - 1 | Fenay Bridge FC |
| 10/25/2008 | Fenay Bridge FC | P - P | Farnley Terriers |
| 11/01/2008 | Fenay Bridge FC | 4 - 3 | Flockton FC |
| 11/08/2008 | Fenay Bridge FC | 4 - 3 | Hade Edge |
| 11/15/2008 | Fenay Bridge FC | 3 - 4 | Royal Dolphins |
| 11/22/2008 | Marsden | 0 - 3 | Fenay Bridge FC |
| 11/29/2008 | Flockton FC | 1 - 3 | Fenay Bridge FC |
| 01/03/2009 | Dewsbury Town OB | 5 - 0 | Fenay Bridge FC |
| 01/17/2009 | Fenay Bridge FC | 4 - 2 | Coach and Horses |
| 01/24/2009 | Fenay Bridge FC | 2 - 0 | Marsden |
| 02/21/2009 | Fenay Bridge FC | 0 - 3 | Dewsbury Town OB |
| Groom Cup Round Two | |||
| 02/28/2009 | Fenay Bridge FC | 7 - 0 | Linthwaite Athletic |
| 03/07/2009 | Royal Dolphins | 3 - 4 | Fenay Bridge FC |
| 03/14/2009 | Cartworth Moor | 2 - 3 | Fenay Bridge FC |
| 03/21/2009 | Farnley Terriers | 1 - 2 | Fenay Bridge FC |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Heyside FC | 10 - 3 | Fenay Bridge FC |