| Secretary | Shirt Colour | Shorts Colour |
| Paul Berry | Royal Blue | Royal Blue |
| Field : West Fields Park | ||
| Division One | |||
| 05/09/2009 | Wooldale Wanderers | 1 - 5 | Meltham Athletic |
| 12/09/2009 | Wooldale Wanderers | 0 - 8 | Hepworth Utd |
| 19/09/2009 | Meltham Athletic | 1 - 0 | Wooldale Wanderers |
| 26/09/2009 | Wooldale Wanderers | 0 - 9 | Newsome WMC |
| 03/10/2009 | Diggle | 3 - 0 | Wooldale Wanderers |
| Sheffield Challenge Cup Round One | |||
| 10/10/2009 | Wooldale Wanderers | 1 - 2 | Millmoor Juniors |
| 17/10/2009 | Wooldale Wanderers | 1 - 5 | Shepley |
| 24/10/2009 | Wooldale Wanderers | 2 - 4 | Diggle |
| 31/10/2009 | Moldgreen | 5 - 1 | Wooldale Wanderers |
| 14/11/2009 | Wooldale Wanderers | 1 - 1 | Heywood Irish Centre FC |
| 28/11/2009 | Cumberworth | 5 - 2 | Wooldale Wanderers |
| 05/12/2009 | Wooldale Wanderers | 2 - 3 | Britannia Sports |
| 23/01/2010 | Uppermill | 2 - 0 | Wooldale Wanderers |
| 06/02/2010 | Wooldale Wanderers | 2 - 2 | Cumberworth |
| 13/02/2010 | Lepton Highlanders | 9 - 2 | Wooldale Wanderers |
| FA Challenge Cup Round Two | |||
| 20/02/2010 | Wooldale Wanderers | 2 - 3 | New Mill 94 |
| 27/02/2010 | Heywood Irish Centre FC | 2 - 2 | Wooldale Wanderers |
| Barlow Cup Round Two | |||
| 06/03/2010 | Hepworth Utd | 3 - 0 | Wooldale Wanderers |
| 20/03/2010 | Wooldale Wanderers | 1 - 5 | Lepton Highlanders |
| 27/03/2010 | Shepley | Void | Wooldale Wanderers |
| 03/04/2010 | Britannia Sports | 7 - 0 | Wooldale Wanderers |
| 10/04/2010 | Wooldale Wanderers | 0 - 1 | Uppermill |
| 13/04/2010 | Wooldale Wanderers | 0 - 2 | Moldgreen |
| 17/04/2010 | Newsome WMC | 7 - 1 | Wooldale Wanderers |
| 24/04/2010 | Hepworth Utd | 6 - 3 | Wooldale Wanderers |