| Reserve Division One | |||
| 09/06/2008 | Britannia Sports Res | 2 - 4 | Uppermill Res |
| 09/13/2008 | Uppermill Res | 5 - 0 | Honley Res |
| 09/20/2008 | Uppermill Res | 5 - 1 | Diggle Res |
| 09/27/2008 | Uppermill Res | 2 - 0 | Kirkheaton Rovers Res |
| 10/04/2008 | Uppermill Res | 3 - 1 | Lepton Highlanders Res |
| FA Junior Cup Round One | |||
| 10/18/2008 | Uppermill Res | 10 - 1 | Heyside FC Res |
| 10/25/2008 | Lepton Highlanders Res | 2 - 2 | Uppermill Res |
| 11/01/2008 | Uppermill Res | 3 - 4 | Netherton Res |
| Richardson Cup Round One | |||
| 11/08/2008 | Honley Res | 2 - 4 | Uppermill Res |
| FA Junior Cup Round Two | |||
| 11/15/2008 | Netherton 'A' | 5 - 6 | Uppermill Res |
| 11/22/2008 | Newsome WMC Res | 5 - 4 | Uppermill Res |
| FA Junior Cup Round Three Quarter Finals | |||
| 12/20/2008 | Uppermill Res | 0 - 1 | Meltham Athletic Res |
| 01/03/2009 | Honley Res | 1 - 4 | Uppermill Res |
| 01/17/2009 | Meltham Athletic Res | 1 - 1 | Uppermill Res |
| 01/31/2009 | Kirkheaton Rovers Res | 2 - 0 | Uppermill Res |
| 02/21/2009 | Uppermill Res | 8 - 0 | Britannia Sports Res |
| Richardson Cup Round Two | |||
| 02/28/2009 | Uppermill Res | 1 - 2 | Diggle A |
| 03/07/2009 | Uppermill Res | 3 - 1 | Newsome WMC Res |
| 03/14/2009 | Berry Brow Lib Res | 5 - 5 | Uppermill Res |
| 03/21/2009 | Uppermill Res | 2 - 1 | Heywood Irish Centre Res |
| 03/28/2009 | Netherton Res | 2 - 2 | Uppermill Res |
| 04/11/2009 | Heywood Irish Centre Res | 1 - 1 | Uppermill Res |
| 04/18/2009 | Uppermill Res | 3 - 1 | Berry Brow Lib Res |
| 05/02/2009 | Diggle Res | 5 - 1 | Uppermill Res |
| 05/09/2009 | Uppermill Res | 2 - 3 | Meltham Athletic Res |