| Division One | |||
| 09/13/2008 | Shepley | 4 - 0 | Wooldale Wanderers |
| 09/20/2008 | Wooldale Wanderers | 2 - 1 | New Mill 94 |
| 10/04/2008 | Wooldale Wanderers | 1 - 4 | Uppermill |
| Sheffield Challenge Cup Round One | |||
| 10/11/2008 | Wooldale Wanderers | 0 - 6 | Hallam |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Wooldale Wanderers | 0 - 6 | Storths Hall (WR) |
| 11/01/2008 | Lepton Highlanders | 4 - 1 | Wooldale Wanderers |
| 11/15/2008 | Wooldale Wanderers | 1 - 1 | Shepley |
| 11/22/2008 | Wooldale Wanderers | 1 - 2 | Lepton Highlanders |
| 11/29/2008 | Newsome WMC | 0 - 1 | Wooldale Wanderers |
| 12/06/2008 | Wooldale Wanderers | 1 - 4 | Britannia Sports |
| Barlow Cup Round Two | |||
| 12/13/2008 | Scholes | 6 - 7 | Wooldale Wanderers |
| 12/20/2008 | Meltham Athletic | 4 - 1 | Wooldale Wanderers |
| 01/03/2009 | Wooldale Wanderers | 1 - 2 | Diggle |
| 01/17/2009 | Wooldale Wanderers | 0 - 2 | Heywood Irish Centre FC |
| 01/24/2009 | Hepworth Utd | 5 - 4 | Wooldale Wanderers |
| 02/21/2009 | Heywood Irish Centre FC | 1 - 1 | Wooldale Wanderers |
| Barlow Cup Round Three Quarter Final | |||
| 02/28/2009 | Honley | 5 - 4 | Wooldale Wanderers |
| 03/14/2009 | Uppermill | 1 - 4 | Wooldale Wanderers |
| 03/21/2009 | Wooldale Wanderers | 1 - 4 | Newsome WMC |
| 03/28/2009 | Wooldale Wanderers | 0 - 2 | Meltham Athletic |
| 04/04/2009 | Diggle | 1 - 0 | Wooldale Wanderers |
| 04/11/2009 | New Mill 94 | 1 - 1 | Wooldale Wanderers |
| 04/18/2009 | Wooldale Wanderers | 1 - 1 | Hepworth Utd |
| 04/25/2009 | Britannia Sports | 7 - 2 | Wooldale Wanderers |