| Division Three | |||
| 09/13/2008 | Shelley | 0 - 2 | Holmbridge |
| 09/20/2008 | Holmbridge | 3 - 4 | Paddock Rangers |
| 09/27/2008 | Heyside FC | 1 - 2 | Holmbridge |
| 10/04/2008 | Holmbridge | 1 - 0 | H.V.Academicals |
| Sheffield Junior Challenge Cup Round One | |||
| 10/11/2008 | Holmbridge | P - P | Oxspring United |
| 10/18/2008 | Upperthong | 2 - 2 | Holmbridge |
| 10/25/2008 | Holmbridge | 2 - 1 | Brook Motors |
| 11/01/2008 | Skelmanthorpe | 4 - 4 | Holmbridge |
| Sheffield Junior Challenge Cup Round Three | |||
| 11/08/2008 | Holmbridge | 4 - 5 | Dodworth Miners |
| 11/15/2008 | H.V.Academicals | 2 - 2 | Holmbridge |
| 11/22/2008 | Holmbridge | 2 - 1 | Dalton Crusaders |
| 11/29/2008 | Grange Moor | 6 - 0 | Holmbridge |
| 12/20/2008 | Lindley AFC | 4 - 5 | Holmbridge |
| 01/03/2009 | Holmbridge | 5 - 1 | Lindley AFC |
| 01/31/2009 | Holmbridge | 2 - 0 | Shelley |
| 02/21/2009 | Holmbridge | 6 - 1 | Heyside FC |
| Groom Cup Round One | |||
| 02/28/2009 | Dalton Crusaders | 0 - 5 | Holmbridge |
| 03/07/2009 | Brook Motors | 0 - 1 | Holmbridge |
| Groom Cup Round Two | |||
| 03/14/2009 | Holmbridge | 1 - 2 | Hade Edge |
| 03/21/2009 | Paddock Rangers | 1 - 1 | Holmbridge |
| 04/04/2009 | Scissett | 3 - 1 | Holmbridge |
| 04/07/2009 | Holmbridge | 6 - 1 | Linthwaite Athletic |
| 04/11/2009 | Holmbridge | 1 - 3 | Scissett |
| 04/18/2009 | Y.M.C.A. | 2 - 1 | Holmbridge |
| 04/21/2009 | Holmbridge | 2 - 2 | Upperthong |
| 04/23/2009 | Linthwaite Athletic | 6 - 4 | Holmbridge |
| 04/25/2009 | Holmbridge | 2 - 3 | Y.M.C.A. |
| 04/28/2009 | Holmbridge | 1 - 4 | Skelmanthorpe |
| 05/02/2009 | Dalton Crusaders | P - P | Holmbridge |
| 05/05/2009 | Holmbridge | 6 - 4 | Grange Moor |