| Division One | |||
| 03/09/2005 | Wooldale Wanderers | 0 - 0 | Meltham Athletic |
| Sheffield Junior Challenge Cup Round One | |||
| 10/09/2005 | Wooldale Wanderers | 4 - 2 | Grange Moor |
| 17/09/2005 | Wooldale Wanderers | 3 - 5 | Diggle |
| 24/09/2005 | Grange Moor | 1 - 1 | Wooldale Wanderers |
| 01/10/2005 | Wooldale Wanderers | 2 - 3 | Sovereign Sports |
| Sheffield Junior Challenge Cup Round Two | |||
| 08/10/2005 | Wooldale Wanderers | P - P | Norwich Union |
| FA Challenge Cup Round One | |||
| 15/10/2005 | Space FC | 4 - 1 | Wooldale Wanderers |
| 22/10/2005 | Wooldale Wanderers | 0 - 5 | Lepton Highlanders |
| 29/10/2005 | Britannia Sports | 1 - 2 | Wooldale Wanderers |
| 05/11/2005 | New Mill 94 | 1 - 0 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Three | |||
| 12/11/2005 | Wooldale Wanderers | 2 - 1 | Stocksbridge Park |
| Barlow Cup Round One | |||
| 19/11/2005 | Wooldale Wanderers | 2 - 2 | Honley |
| 26/11/2005 | Wooldale Wanderers | 1 - 1 | Shepley |
| 03/12/2005 | Meltham Athletic | 2 - 3 | Wooldale Wanderers |
| Sheffield Junior Challenge Cup Round Four | |||
| 10/12/2005 | Kinsley Boys | 3 - 1 | Wooldale Wanderers |
| 07/01/2006 | Diggle | 1 - 4 | Wooldale Wanderers |
| Barlow Cup Round One | |||
| 14/01/2006 | Honley | 4 - 2 | Wooldale Wanderers |
| 21/01/2006 | Wooldale Wanderers | 3 - 3 | Honley |
| 28/01/2006 | Wooldale Wanderers | 8 - 2 | Grange Moor |
| 04/02/2006 | Honley | 2 - 2 | Wooldale Wanderers |
| 11/02/2006 | Wooldale Wanderers | 2 - 1 | Heywood Sports |
| 18/02/2006 | Lepton Highlanders | 2 - 1 | Wooldale Wanderers |
| 25/02/2006 | Sovereign Sports | 2 - 2 | Wooldale Wanderers |
| 18/03/2006 | Wooldale Wanderers | 2 - 2 | Uppermill |
| 08/04/2006 | Wooldale Wanderers | 4 - 0 | New Mill 94 |
| 15/04/2006 | Uppermill | 0 - 0 | Wooldale Wanderers |
| 22/04/2006 | Wooldale Wanderers | 0 - 1 | Britannia Sports |
| 25/04/2006 | Heywood Sports | 2 - 1 | Wooldale Wanderers |
| 29/04/2006 | Shepley | 3 - 2 | Wooldale Wanderers |