| Division Four | |||
| 09/13/2008 | Royal Dolphins | 8 - 5 | Dewsbury Town OB |
| 09/27/2008 | Dewsbury Town OB | 8 - 1 | Farnley Terriers |
| 10/04/2008 | Hade Edge | 4 - 2 | Dewsbury Town OB |
| Heavy Woollen District FA Cup | |||
| 10/18/2008 | Hunsworth | 3 - 0 | Dewsbury Town OB |
| 10/25/2008 | Flockton FC | 0 - 0 | Dewsbury Town OB |
| 11/01/2008 | Dewsbury Town OB | 3 - 2 | Hade Edge |
| 11/15/2008 | Dewsbury Town OB | 13 - 0 | Marsden |
| 11/22/2008 | Cartworth Moor | 2 - 0 | Dewsbury Town OB |
| 11/29/2008 | Dewsbury Town OB | 5 - 3 | Coach and Horses |
| 12/06/2008 | Dewsbury Town OB | 5 - 0 | Flockton FC |
| 01/03/2009 | Dewsbury Town OB | 5 - 0 | Fenay Bridge FC |
| 01/17/2009 | Farnley Terriers | 2 - 5 | Dewsbury Town OB |
| 02/21/2009 | Fenay Bridge FC | 0 - 3 | Dewsbury Town OB |
| Groom Cup Round One | |||
| 02/28/2009 | Flockton FC | 0 - 3 | Dewsbury Town OB |
| 03/07/2009 | Marsden | 1 - 4 | Dewsbury Town OB |
| Groom Cup Round Two | |||
| 03/14/2009 | Dewsbury Town OB | P - P | Marsden |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | H.V.Academicals | 1 - 2 | Dewsbury Town OB |
| 04/04/2009 | Coach and Horses | 1 - 2 | Dewsbury Town OB |
| 04/11/2009 | Dewsbury Town OB | 6 - 1 | Cartworth Moor |
| Groom Cup Semi Final | |||
| 04/13/2009 | Dewsbury Town OB | 2 - 3 | Skelmanthorpe |
| 04/18/2009 | Dewsbury Town OB | 2 - 0 | Royal Dolphins |