| Division One |
| 05/09/2009 |
Cumberworth |
1 - 2 |
Britannia Sports |
| 19/09/2009 |
Diggle |
2 - 2 |
Cumberworth |
| 26/09/2009 |
Cumberworth |
3 - 0 |
Heywood Irish Centre FC |
| 03/10/2009 |
Lepton Highlanders |
1 - 0 |
Cumberworth |
| Sheffield Junior Challenge Cup Round One |
| 10/10/2009 |
Telecom Sports |
1 - 2 |
Cumberworth |
| FA Challenge Cup Round One |
| 17/10/2009 |
Cumberworth |
5 - 1 |
Brook Motors |
| 24/10/2009 |
Newsome WMC |
2 - 0 |
Cumberworth |
| 31/10/2009 |
Cumberworth |
1 - 3 |
Shepley |
| Sheffield Junior Challenge Cup Round Two |
| 14/11/2009 |
Grange Moor |
2 - 3 |
Cumberworth |
| 28/11/2009 |
Cumberworth |
5 - 2 |
Wooldale Wanderers |
| 05/12/2009 |
Hepworth Utd |
2 - 1 |
Cumberworth |
| Sheffield Junior Challenge Cup Round Three |
| 12/12/2009 |
Cumberworth |
1 - 2 |
TBA |
| Barlow Cup Round One |
| 23/01/2010 |
Kirkheaton Rovers |
0 - 2 |
Cumberworth |
| FA Challenge Cup Round Two |
| 30/01/2010 |
Scholes |
1 - 0 |
Cumberworth |
| 06/02/2010 |
Wooldale Wanderers |
2 - 2 |
Cumberworth |
| Barlow Cup Round Two |
| 13/02/2010 |
Honley |
6 - 1 |
Cumberworth |
| 20/02/2010 |
Cumberworth |
1 - 2 |
Uppermill |
| 06/03/2010 |
Cumberworth |
0 - 0 |
Meltham Athletic |
| 13/03/2010 |
Britannia Sports |
1 - 3 |
Cumberworth |
| 20/03/2010 |
Cumberworth |
3 - 1 |
Moldgreen |
| 27/03/2010 |
Moldgreen |
1 - 2 |
Cumberworth |
| 03/04/2010 |
Cumberworth |
1 - 0 |
Hepworth Utd |
| 10/04/2010 |
Cumberworth |
0 - 1 |
Newsome WMC |
| 13/04/2010 |
Meltham Athletic |
0 - 0 |
Cumberworth |
| 17/04/2010 |
Heywood Irish Centre FC |
4 - 1 |
Cumberworth |
| 20/04/2010 |
Cumberworth |
1 - 1 |
Lepton Highlanders |
| 24/04/2010 |
Cumberworth |
2 - 3 |
Diggle |
| 29/04/2010 |
Shepley |
3 - 1 |
Cumberworth |
| 01/05/2010 |
Uppermill |
1 - 1 |
Cumberworth |