| Sheffield Junior Challenge Cup Round One | |||
| Sheffield Junior Challenge Cup Round One | |||
| 08/09/2007 | Wooldale Wanderers | 2 - 1 | Nostell MW FC |
| 15/09/2007 | Wooldale Wanderers | 3 - 1 | Lepton Highlanders |
| 22/09/2007 | New Mill 94 | 2 - 2 | Wooldale Wanderers |
| 29/09/2007 | Wooldale Wanderers | 1 - 1 | Newsome WMC |
| 06/10/2007 | Britannia Sports | 1 - 1 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round One | |||
| 13/10/2007 | Wooldale Wanderers | 4 - 1 | Sheffield Medics |
| FA Challenge Cup Round One | |||
| 20/10/2007 | Wooldale Wanderers | 3 - 0 | Aimbry |
| 27/10/2007 | Slaithwaite Utd | 0 - 3 | Wooldale Wanderers |
| 03/11/2007 | Diggle | 1 - 0 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Two | |||
| 10/11/2007 | Wooldale Wanderers | 4 - 3 | Farm Road S&SC |
| FA Challenge Cup Round Two | |||
| 17/11/2007 | Fenay Bridge | 3 - 4 | Wooldale Wanderers |
| 24/11/2007 | Wooldale Wanderers | 6 - 1 | Meltham Athletic |
| 01/12/2007 | Aimbry | 1 - 1 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Three | |||
| 08/12/2007 | Wooldale Wanderers | 1 - 2 | Aston FC |
| 22/12/2007 | Wooldale Wanderers | 3 - 1 | Diggle |
| 05/01/2008 | Lepton Highlanders | 3 - 2 | Wooldale Wanderers |
| Barlow Cup Round One | |||
| 12/01/2008 | Berry Brow Lib | 3 - 2 | Wooldale Wanderers |
| 09/02/2008 | Wooldale Wanderers | 5 - 4 | Britannia Sports |
| FA Challenge Cup Round Three | |||
| 23/02/2008 | Diggle | 2 - 3 | Wooldale Wanderers |
| 08/03/2008 | Meltham Athletic | 0 - 0 | Wooldale Wanderers |
| FA Challenge Cup Round Four Quarter Final | |||
| 15/03/2008 | Newsome WMC | 5 - 2 | Wooldale Wanderers |
| 22/03/2008 | Wooldale Wanderers | 1 - 1 | New Mill 94 |
| 29/03/2008 | Heywood Irish Centre FC | 1 - 0 | Wooldale Wanderers |
| 05/04/2008 | Wooldale Wanderers | 2 - 1 | Uppermill |
| 08/04/2008 | Wooldale Wanderers | 1 - 2 | Heywood Irish Centre FC |
| 19/04/2008 | Wooldale Wanderers | 2 - 2 | Shepley |
| 22/04/2008 | Newsome WMC | P - P | Wooldale Wanderers |
| 26/04/2008 | Shepley | 0 - 0 | Wooldale Wanderers |
| 29/04/2008 | Wooldale Wanderers | P - P | Aimbry |
| 03/05/2008 | Wooldale Wanderers | 2 - 3 | Slaithwaite Utd |
| 06/05/2008 | Uppermill | 0 - 4 | Wooldale Wanderers |