| Division Three | |||
| 09/13/2008 | Y.M.C.A. | 7 - 1 | Skelmanthorpe |
| 09/20/2008 | Shelley | 1 - 6 | Y.M.C.A. |
| 09/27/2008 | Y.M.C.A. | 1 - 4 | Dalton Crusaders |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Knaresborough Town | 4 - 0 | Y.M.C.A. |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Brook Motors | 1 - 3 | Y.M.C.A. |
| 10/25/2008 | Heyside FC | 1 - 4 | Y.M.C.A. |
| 11/01/2008 | Y.M.C.A. | 2 - 0 | Linthwaite Athletic |
| Groom Cup Round One | |||
| 11/08/2008 | Y.M.C.A. | 4 - 0 | Royal Dolphins |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | Y.M.C.A. | 1 - 4 | Bay Athletic (WR) |
| 11/22/2008 | H.V.Academicals | 0 - 1 | Y.M.C.A. |
| 11/29/2008 | Y.M.C.A. | 2 - 2 | Scissett |
| Groom Cup Round Two | |||
| 12/13/2008 | Heyside FC | 3 - 1 | Y.M.C.A |
| 12/20/2008 | Brook Motors | 2 - 7 | Y.M.C.A. |
| 01/03/2009 | Y.M.C.A. | 3 - 0 | Brook Motors |
| 01/24/2009 | Y.M.C.A. | 8 - 0 | Heyside FC |
| 01/31/2009 | Skelmanthorpe | 1 - 5 | Y.M.C.A. |
| 02/21/2009 | Y.M.C.A. | 4 - 1 | Lindley AFC |
| 02/28/2009 | Y.M.C.A. | 4 - 1 | Upperthong |
| 03/07/2009 | Lindley AFC | 0 - 1 | Y.M.C.A. |
| 03/21/2009 | Y.M.C.A. | 2 - 0 | Shelley |
| 03/28/2009 | Dalton Crusaders | 0 - 2 | Y.M.C.A. |
| 04/04/2009 | Y.M.C.A. | 1 - 1 | Grange Moor |
| 04/07/2009 | Scissett | 2 - 1 | Y.M.C.A. |
| 04/11/2009 | Paddock Rangers | 2 - 2 | Y.M.C.A. |
| 04/14/2009 | Upperthong | 1 - 1 | Y.M.C.A. |
| 04/16/2009 | Grange Moor | 0 - 2 | Y.M.C.A. |
| 04/18/2009 | Y.M.C.A. | 2 - 1 | Holmbridge |
| 04/21/2009 | Y.M.C.A. | 2 - 2 | Paddock Rangers |
| 04/25/2009 | Holmbridge | 2 - 3 | Y.M.C.A. |
| 04/30/2009 | Linthwaite Athletic | 2 - 1 | Y.M.C.A. |
| 05/02/2009 | Y.M.C.A. | 1 - 1 | H.V.Academicals |