| Secretary | Shirt Colour | Shorts Colour |
| Paul Berry | Royal Blue | Royal Blue |
| Field : West Fields Park | ||
| Reserve Division Two | |||
| 05/09/2009 | Upperthong Res | 9 - 0 | Wooldale Wanderers Res |
| 12/09/2009 | Uppermill 'A' | 9 - 0 | Wooldale Wanderers Res |
| 19/09/2009 | Wooldale Wanderers Res | 1 - 3 | Slaithwaite Utd Res |
| 26/09/2009 | Westend Res | 5 - 2 | Wooldale Wanderers Res |
| 10/10/2009 | Honley Res | 2 - 0 | Wooldale Wanderers Res |
| FA Junior Cup Round One | |||
| 17/10/2009 | Honley Res | 2 - 8 | Wooldale Wanderers Res |
| 24/10/2009 | Diggle A | 8 - 0 | Wooldale Wanderers Res |
| 31/10/2009 | Wooldale Wanderers Res | 4 - 1 | Mount Res |
| 07/11/2009 | Wooldale Wanderers Res | 6 - 4 | Heyside FC Res |
| 05/12/2009 | Scholes Res | 5 - 3 | Wooldale Wanderers Res |
| Richardson Cup Round Two | |||
| 12/12/2009 | Wooldale Wanderers Res | 5 - 3 | Kirkheaton Rovers Res |
| 23/01/2010 | Wooldale Wanderers Res | 1 - 3 | Uppermill 'A' |
| 06/02/2010 | Heyside FC Res | 1 - 1 | Wooldale Wanderers Res |
| Richardson Cup Round Three Quarter Final | |||
| 13/02/2010 | Wooldale Wanderers Res | 2 - 5 | Lepton Highlanders Res |
| FA Junior Cup Round Two | |||
| 20/02/2010 | Lepton Highlanders Res | 10 - 4 | Wooldale Wanderers Res |
| 06/03/2010 | Wooldale Wanderers Res | 3 - 1 | Meltham Athletic 'A' |
| 13/03/2010 | Meltham Athletic 'A' | 1 - 3 | Wooldale Wanderers Res |
| 20/03/2010 | Slaithwaite Utd Res | Void | Wooldale Wanderers Res |
| 27/03/2010 | Wooldale Wanderers Res | 3 - 3 | Honley Res |
| 03/04/2010 | Wooldale Wanderers Res | 4 - 1 | Upperthong Res |
| 13/04/2010 | New Mill 94 Res | 2 - 4 | Wooldale Wanderers Res |
| 17/04/2010 | Wooldale Wanderers Res | 0 - 7 | Westend Res |
| 24/04/2010 | Wooldale Wanderers Res | Void | Scholes Res |
| 27/04/2010 | Wooldale Wanderers Res | 1 - 1 | Diggle A |
| 29/04/2010 | Wooldale Wanderers Res | 1 - 0 | New Mill 94 Res |
| 01/05/2010 | Mount Res | 3 - 2 | Wooldale Wanderers Res |