| Division Three | |||
| 09/13/2008 | Upperthong | 3 - 2 | Grange Moor |
| 09/20/2008 | Linthwaite Athletic | 2 - 2 | Upperthong |
| 09/27/2008 | Upperthong | 1 - 3 | Scissett |
| 10/04/2008 | Lindley AFC | 0 - 8 | Upperthong |
| 10/11/2008 | H.V.Academicals | 2 - 2 | Upperthong |
| 10/18/2008 | Upperthong | 2 - 2 | Holmbridge |
| 10/25/2008 | Shelley | 2 - 2 | Upperthong |
| 11/08/2008 | Brook Motors | 2 - 3 | Upperthong |
| 11/22/2008 | Heyside FC | 6 - 0 | Upperthong |
| FA Challenge Cup Round Two | |||
| 12/20/2008 | Golcar Utd | 6 - 0 | Upperthong |
| 01/03/2009 | Upperthong | 1 - 3 | Skelmanthorpe |
| 01/17/2009 | Dalton Crusaders | 3 - 2 | Upperthong |
| Groom Cup Round Two | |||
| 01/24/2009 | Upperthong | 0 - 2 | Shelley |
| 01/31/2009 | Scissett | 1 - 2 | Upperthong |
| 02/21/2009 | Upperthong | 0 - 0 | Paddock Rangers |
| 02/28/2009 | Y.M.C.A. | 4 - 1 | Upperthong |
| 03/07/2009 | Upperthong | 3 - 0 | Shelley |
| 03/14/2009 | Paddock Rangers | 2 - 2 | Upperthong |
| 03/21/2009 | Upperthong | 1 - 0 | Lindley AFC |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Skelmanthorpe | 2 - 1 | Upperthong |
| 04/04/2009 | Upperthong | 3 - 2 | Linthwaite Athletic |
| 04/09/2009 | Skelmanthorpe | 5 - 2 | Upperthong |
| 04/11/2009 | Grange Moor | 0 - 1 | Upperthong |
| 04/14/2009 | Upperthong | 1 - 1 | Y.M.C.A. |
| 04/21/2009 | Holmbridge | 2 - 2 | Upperthong |
| 04/25/2009 | Upperthong | 0 - 1 | H.V.Academicals |
| 04/28/2009 | Upperthong | 2 - 4 | Heyside FC |
| 05/02/2009 | Upperthong | 5 - 3 | Brook Motors |
| 05/05/2009 | Upperthong | 1 - 3 | Dalton Crusaders |