| Division Three | |||
| 09/13/2008 | Paddock Rangers | 5 - 4 | Lindley AFC |
| 09/20/2008 | Holmbridge | 3 - 4 | Paddock Rangers |
| 09/27/2008 | Paddock Rangers | 1 - 1 | Shelley |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Paddock Rangers | 2 - 0 | Bingley Town |
| 10/11/2008 | Heyside FC | 2 - 3 | Paddock Rangers |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Newsome WMC | 0 - 1 | Paddock Rangers |
| 10/25/2008 | Paddock Rangers | 0 - 0 | H.V.Academicals |
| West Riding Challenge Trophy Round Two | |||
| 11/01/2008 | Paddock Rangers | 1 - 3 | Ovenden West Riding |
| 11/08/2008 | Paddock Rangers | 7 - 2 | Linthwaite Athletic |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | Paddock Rangers | 2 - 8 | Heywood Irish Centre FC |
| 11/22/2008 | Paddock Rangers | 3 - 5 | Brook Motors |
| 11/29/2008 | Skelmanthorpe | 7 - 2 | Paddock Rangers |
| 12/06/2008 | Paddock Rangers | 2 - 2 | Dalton Crusaders |
| 12/20/2008 | Dalton Crusaders | 4 - 2 | Paddock Rangers |
| 01/03/2009 | Linthwaite Athletic | 2 - 2 | Paddock Rangers |
| 01/17/2009 | Scissett | 1 - 0 | Paddock Rangers |
| Groom Cup Round One | |||
| 01/24/2009 | Paddock Rangers | 1 - 3 | Grange Moor |
| 01/31/2009 | Lindley AFC | 4 - 3 | Paddock Rangers |
| 02/21/2009 | Upperthong | 0 - 0 | Paddock Rangers |
| 02/28/2009 | Paddock Rangers | 0 - 1 | Skelmanthorpe |
| 03/07/2009 | H.V.Academicals | 1 - 2 | Paddock Rangers |
| 03/14/2009 | Paddock Rangers | 2 - 2 | Upperthong |
| 03/21/2009 | Paddock Rangers | 1 - 1 | Holmbridge |
| 03/28/2009 | Paddock Rangers | 2 - 3 | Scissett |
| 04/04/2009 | Brook Motors | 2 - 1 | Paddock Rangers |
| 04/11/2009 | Paddock Rangers | 2 - 2 | Y.M.C.A. |
| 04/18/2009 | Shelley | 3 - 3 | Paddock Rangers |
| 04/21/2009 | Y.M.C.A. | 2 - 2 | Paddock Rangers |
| 04/25/2009 | Grange Moor | 0 - 2 | Paddock Rangers |
| 05/02/2009 | Paddock Rangers | 2 - 1 | Grange Moor |
| 05/05/2009 | Paddock Rangers | 0 - 2 | Heyside FC |