| Reserve Division One | |||
| 09/13/2008 | Britannia Sports Res | 4 - 2 | Diggle Res |
| 09/20/2008 | Uppermill Res | 5 - 1 | Diggle Res |
| 09/27/2008 | Heywood Irish Centre Res | 1 - 6 | Diggle Res |
| 10/11/2008 | Newsome WMC Res | 0 - 1 | Diggle Res |
| 10/25/2008 | Diggle Res | 3 - 1 | Berry Brow Lib Res |
| 11/01/2008 | Honley Res | 3 - 5 | Diggle Res |
| Richardson Cup Round One | |||
| 11/08/2008 | Diggle Res | 0 - 2 | Newsome WMC Res |
| FA Junior Cup Round One | |||
| 11/15/2008 | Cartworth Moor Res | 2 - 8 | Diggle Res |
| 11/22/2008 | Diggle Res | 2 - 1 | Kirkheaton Rovers Res |
| 11/29/2008 | Diggle Res | 1 - 2 | Meltham Athletic Res |
| 01/03/2009 | Berry Brow Lib Res | 1 - 2 | Diggle Res |
| FA Junior Cup Round Two | |||
| 01/17/2009 | Diggle Res | 8 - 0 | KKS Ashbrow Res |
| 01/24/2009 | Netherton Res | 1 - 2 | Diggle Res |
| 01/31/2009 | Diggle Res | 4 - 3 | Heywood Irish Centre Res |
| 02/21/2009 | Kirkheaton Rovers Res | 2 - 1 | Diggle Res |
| FA Junior Cup Round Three Quarter Finals | |||
| 02/28/2009 | Netherton Res | 2 - 0 | Diggle Res |
| 03/14/2009 | Meltham Athletic Res | 0 - 4 | Diggle Res |
| 03/21/2009 | Diggle Res | 1 - 4 | Lepton Highlanders Res |
| 03/28/2009 | Diggle Res | 4 - 1 | Honley Res |
| 04/09/2009 | Diggle Res | 3 - 0 | Newsome WMC Res |
| 04/11/2009 | Diggle Res | 3 - 0 | Britannia Sports Res |
| 04/25/2009 | Lepton Highlanders Res | 0 - 4 | Diggle Res |
| 04/28/2009 | Diggle Res | 3 - 1 | Netherton Res |
| 05/02/2009 | Diggle Res | 5 - 1 | Uppermill Res |