| Reserve Division One | |||
| 09/13/2008 | Heywood Irish Centre Res | 0 - 2 | Meltham Athletic Res |
| 09/20/2008 | Britannia Sports Res | 0 - 1 | Heywood Irish Centre Res |
| 09/27/2008 | Heywood Irish Centre Res | 1 - 6 | Diggle Res |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Mount | 2 - 4 | Heywood Irish Centre FC Res |
| 10/11/2008 | Lepton Highlanders Res | 3 - 3 | Heywood Irish Centre Res |
| 10/25/2008 | Heywood Irish Centre Res | 2 - 1 | Newsome WMC Res |
| West Riding Challenge Trophy Round Two | |||
| 11/01/2008 | Heywood Irish Centre Res | 4 - 5 | Bardsey Res |
| FA Junior Cup Round One | |||
| 11/15/2008 | Heywood Irish Centre Res | 2 - 1 | Slaithwaite Utd Res |
| 11/22/2008 | Heywood Irish Centre Res | 4 - 2 | Honley Res |
| 11/29/2008 | Kirkheaton Rovers Res | 6 - 2 | Heywood Irish Centre Res |
| 12/20/2008 | Heywood Irish Centre Res | 6 - 8 | Kirkheaton Rovers Res |
| 01/03/2009 | Meltham Athletic Res | 3 - 2 | Heywood Irish Centre Res |
| FA Junior Cup Round Two | |||
| 01/17/2009 | Heywood Irish Centre Res | 1 - 2 | Netherton Res |
| Richardson Cup Round One | |||
| 01/24/2009 | Cumberworth Res | 2 - 5 | Heywood Irish Centre Res |
| 01/31/2009 | Diggle Res | 4 - 3 | Heywood Irish Centre Res |
| 02/21/2009 | Berry Brow Lib Res | 1 - 1 | Heywood Irish Centre Res |
| Richardson Cup Round Two | |||
| 02/28/2009 | Mount Res | 0 - 7 | Heywood Irish Centre Res |
| 03/07/2009 | Heywood Irish Centre Res | 2 - 4 | Britannia Sports Res |
| Richardson Cup Round Three Quarter Final | |||
| 03/14/2009 | Shepley Res | 1 - 2 | Heywood Irish Centre Res |
| 03/21/2009 | Uppermill Res | 2 - 1 | Heywood Irish Centre Res |
| 03/28/2009 | Heywood Irish Centre Res | 4 - 2 | Berry Brow Lib Res |
| 04/04/2009 | Honley Res | 0 - 6 | Heywood Irish Centre Res |
| Richardson Cup Semi Final | |||
| 04/07/2009 | Diggle 'A' | 1 - 2 | Heywood Irish Centre Res |
| 04/11/2009 | Heywood Irish Centre Res | 1 - 1 | Uppermill Res |
| 04/18/2009 | Heywood Irish Centre Res | 1 - 3 | Lepton Highlanders Res |
| Richardson Cup Final | |||
| 04/21/2009 | Heywood Irish Centre Res | 4 - 3 | Netherton Res |
| 04/23/2009 | Newsome WMC Res | 8 - 2 | Heywood Irish Centre Res |
| 04/25/2009 | Netherton Res | 3 - 4 | Heywood Irish Centre Res |
| 05/02/2009 | Heywood Irish Centre Res | 3 - 3 | Netherton Res |