| Division Four | |||
| 09/20/2008 | Fenay Bridge FC | 1 - 0 | Cartworth Moor |
| 09/27/2008 | Cartworth Moor | 7 - 1 | Marsden |
| 10/04/2008 | Flockton FC | 4 - 1 | Cartworth Moor |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Cartworth Moor | 2 - 1 | The Furnace |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Cartworth Moor | 3 - 8 | Uppermill |
| 10/25/2008 | Cartworth Moor | 5 - 2 | Royal Dolphins |
| 11/01/2008 | Coach and Horses | 3 - 3 | Cartworth Moor |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/08/2008 | Mosborough Trinity | 4 - 2 | Cartworth Moor |
| 11/15/2008 | Hade Edge | 2 - 3 | Cartworth Moor |
| 11/22/2008 | Cartworth Moor | 2 - 0 | Dewsbury Town OB |
| 12/06/2008 | Cartworth Moor | 5 - 4 | Hade Edge |
| Groom Cup Round One | |||
| 12/13/2008 | Cartworth Moor | 4 - 6 | Brook Motors |
| 12/20/2008 | Cartworth Moor | P - P | Farnley Terriers |
| 01/03/2009 | Marsden | 1 - 6 | Cartworth Moor |
| 01/17/2009 | Cartworth Moor | 3 - 1 | Flockton FC |
| 01/24/2009 | Cartworth Moor | 4 - 1 | Coach and Horses |
| 01/31/2009 | Royal Dolphins | 3 - 1 | Cartworth Moor |
| 02/28/2009 | Farnley Terriers | 2 - 1 | Cartworth Moor |
| 03/14/2009 | Cartworth Moor | 2 - 3 | Fenay Bridge FC |
| 04/11/2009 | Dewsbury Town OB | 6 - 1 | Cartworth Moor |