| Division Three | |||
| 09/13/2008 | Y.M.C.A. | 7 - 1 | Skelmanthorpe |
| 09/20/2008 | Dalton Crusaders | 3 - 3 | Skelmanthorpe |
| 09/27/2008 | Skelmanthorpe | 2 - 2 | Grange Moor |
| 10/04/2008 | Linthwaite Athletic | 2 - 3 | Skelmanthorpe |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Skelmanthorpe | 3 - 1 | Sheffield Medics |
| FA Challenge Cup Round One | |||
| 10/18/2008 | FC Railway | 1 - 3 | Skelmanthorpe |
| 10/25/2008 | Lindley AFC | 0 - 3 | Skelmanthorpe |
| 11/01/2008 | Skelmanthorpe | 4 - 4 | Holmbridge |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/08/2008 | Skelmanthorpe | 7 - 0 | Shelley |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | New Mill 94 | 4 - 3 | Skelmanthorpe |
| 11/22/2008 | Shelley | 2 - 1 | Skelmanthorpe |
| 11/29/2008 | Skelmanthorpe | 7 - 2 | Paddock Rangers |
| Sheffield Junior Challenge Cup Round Four | |||
| 12/20/2008 | Skelmanthorpe | 3 - 2 | Thurock Corinthians |
| 01/03/2009 | Upperthong | 1 - 3 | Skelmanthorpe |
| Sheffield Junior Challenge Cup, Quarter Final | |||
| 01/17/2009 | Telecom Sports | 2 - 1 | Skelmanthorpe |
| 01/31/2009 | Skelmanthorpe | 1 - 5 | Y.M.C.A. |
| 02/21/2009 | Skelmanthorpe | 11 - 0 | Linthwaite Athletic |
| 02/28/2009 | Paddock Rangers | 0 - 1 | Skelmanthorpe |
| 03/07/2009 | Skelmanthorpe | 1 - 0 | Heyside FC |
| Groom Cup Round Two | |||
| 03/14/2009 | Lindley AFC | 1 - 6 | Skelmanthorpe |
| 03/21/2009 | Skelmanthorpe | 3 - 0 | Dalton Crusaders |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Skelmanthorpe | 2 - 1 | Upperthong |
| 04/04/2009 | Skelmanthorpe | 4 - 1 | H.V.Academicals |
| 04/09/2009 | Skelmanthorpe | 5 - 2 | Upperthong |
| 04/11/2009 | Skelmanthorpe | 2 - 1 | Shelley |
| Groom Cup Semi Final | |||
| 04/13/2009 | Dewsbury Town OB | 2 - 3 | Skelmanthorpe |
| 04/16/2009 | Skelmanthorpe | 1 - 0 | Brook Motors |
| 04/18/2009 | Brook Motors | 1 - 3 | Skelmanthorpe |
| 04/21/2009 | Scissett | 3 - 4 | Skelmanthorpe |
| 04/23/2009 | Grange Moor | 0 - 4 | Skelmanthorpe |
| 04/25/2009 | Skelmanthorpe | 0 - 4 | Scissett |
| 04/28/2009 | Holmbridge | 1 - 4 | Skelmanthorpe |
| Groom Cup Final | |||
| 05/01/2009 | Skelmanthorpe | 3 - 4 | Heyside FC |
| 05/05/2009 | Skelmanthorpe | P - P | Lindley AFC |
| 05/07/2009 | H.V.Academicals | 3 - 1 | Skelmanthorpe |
| 05/09/2009 | Heyside FC | 3 - 7 | Skelmanthorpe |