| Division One | |||
| 09/06/2008 | Uppermill | 0 - 1 | Shepley |
| 09/13/2008 | Shepley | 4 - 0 | Wooldale Wanderers |
| 09/20/2008 | Shepley | 0 - 0 | Meltham Athletic |
| 09/27/2008 | New Mill 94 | 0 - 2 | Shepley |
| 10/04/2008 | Shepley | 2 - 3 | Diggle |
| Sheffield Challenge Cup Round One | |||
| 10/11/2008 | Shepley | 3 - 0 | New Mill 94 |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Britannia Sports | 3 - 2 | Shepley |
| 10/25/2008 | Shepley | 3 - 2 | Britannia Sports |
| 11/01/2008 | Hepworth Utd | 0 - 0 | Shepley |
| Sheffield Challenge Cup Round Two | |||
| 11/08/2008 | Kirkburton | 4 - 3 | Shepley |
| 11/15/2008 | Wooldale Wanderers | 1 - 1 | Shepley |
| 11/22/2008 | Shepley | 1 - 1 | Heywood Irish Centre FC |
| 11/29/2008 | Lepton Highlanders | 2 - 0 | Shepley |
| 12/06/2008 | Shepley | 1 - 2 | Newsome WMC |
| 01/17/2009 | Shepley | 1 - 2 | Lepton Highlanders |
| 01/24/2009 | Heywood Irish Centre FC | 2 - 3 | Shepley |
| 01/31/2009 | Shepley | 2 - 1 | New Mill 94 |
| 02/28/2009 | Diggle | 3 - 4 | Shepley |
| 03/07/2009 | Shepley | 3 - 1 | Uppermill |
| Barlow Cup Round Three Quarter Final | |||
| 03/14/2009 | Hepworth Utd | 3 - 1 | Shepley |
| 03/21/2009 | Meltham Athletic | 2 - 1 | Shepley |
| 03/28/2009 | Newsome WMC | 2 - 0 | Shepley |
| 04/04/2009 | Britannia Sports | 4 - 1 | Shepley |
| 04/11/2009 | Shepley | 3 - 2 | Hepworth Utd |