| Reserve Division Two | |||
| 09/20/2008 | New Mill 94 Res | 0 - 3 | Shepley Res |
| 09/27/2008 | Shepley Res | 2 - 2 | Heyside FC Res |
| 10/04/2008 | H.V.Academicals Res | 1 - 9 | Shepley Res |
| FA Junior Cup Round One | |||
| 10/18/2008 | Netherton Res | 2 - 1 | Shepley Res |
| 10/25/2008 | Cumberworth Res | 1 - 2 | Shepley Res |
| 11/01/2008 | Shepley Res | 6 - 1 | Mount Res |
| 11/08/2008 | Shepley Res | 4 - 1 | Westend Res |
| 11/15/2008 | Shepley Res | 5 - 0 | H.V.Academicals Res |
| 11/22/2008 | Scholes Res | 0 - 1 | Shepley Res |
| 12/06/2008 | Westend Res | 3 - 1 | Shepley Res |
| 12/20/2008 | Shepley Res | 3 - 1 | Wooldale Wanderers Res |
| 01/03/2009 | Shepley Res | 6 - 0 | Uppermill 'A' |
| Richardson Cup Round One | |||
| 01/24/2009 | Wooldale Wanderers Res | 1 - 4 | Shepley Res |
| 01/31/2009 | Heyside FC Res | 0 - 3 | Shepley Res |
| 02/21/2009 | Shepley Res | 2 - 0 | Scholes Res |
| Richardson Cup Round Two | |||
| 02/28/2009 | Shepley Res | 4 - 1 | H.V.Academicals Res |
| 03/07/2009 | Wooldale Wanderers Res | P - P | Shepley Res |
| Richardson Cup Round Three Quarter Final | |||
| 03/14/2009 | Shepley Res | 1 - 2 | Heywood Irish Centre Res |
| 03/21/2009 | Shepley Res | 0 - 4 | Cumberworth Res |
| 03/28/2009 | Mount Res | 0 - 5 | Shepley Res |
| 04/04/2009 | Shepley Res | 4 - 1 | Slaithwaite Utd Res |
| 04/09/2009 | Uppermill 'A' | 2 - 1 | Shepley Res |
| 04/16/2009 | Slaithwaite Utd Res | 0 - 4 | Shepley Res |
| 04/18/2009 | Shepley Res | 9 - 0 | New Mill 94 Res |
| 04/25/2009 | Shepley Res | 4 - 2 | Diggle A |
| 05/02/2009 | Diggle A | 3 - 5 | Shepley Res |