| Division Three | |||
| 09/13/2008 | Heyside FC | 1 - 3 | Scissett |
| 09/20/2008 | Lindley AFC | 7 - 2 | Heyside FC |
| 09/27/2008 | Heyside FC | 1 - 2 | Holmbridge |
| Manchester County FA Challenge Cup | |||
| 10/04/2008 | Fives Athletic | 0 - 4 | Heyside FC |
| 10/11/2008 | Heyside FC | 2 - 3 | Paddock Rangers |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Heyside FC | 2 - 3 | Lepton Highlanders |
| 10/25/2008 | Heyside FC | 1 - 4 | Y.M.C.A. |
| 11/01/2008 | H.V.Academicals | 5 - 4 | Heyside FC |
| Manchester County FA Challenge Cup | |||
| 11/08/2008 | Chorltonians | 1 - 0 | Heyside FC |
| 11/15/2008 | Heyside FC | 3 - 2 | Lindley AFC |
| 11/22/2008 | Heyside FC | 6 - 0 | Upperthong |
| 11/29/2008 | Brook Motors | 5 - 2 | Heyside FC |
| Groom Cup Round Two | |||
| 12/13/2008 | Heyside FC | 3 - 1 | Y.M.C.A |
| 12/20/2008 | Scissett | 3 - 1 | Heyside FC |
| 01/03/2009 | Heyside FC | 2 - 3 | Grange Moor |
| 01/24/2009 | Y.M.C.A. | 8 - 0 | Heyside FC |
| 01/31/2009 | Grange Moor | P - P | Heyside FC |
| 02/21/2009 | Holmbridge | 6 - 1 | Heyside FC |
| 02/28/2009 | Shelley | 4 - 1 | Heyside FC |
| 03/07/2009 | Skelmanthorpe | 1 - 0 | Heyside FC |
| 03/14/2009 | Heyside FC | 2 - 2 | H.V.Academicals |
| 03/21/2009 | Heyside FC | 4 - 1 | Linthwaite Athletic |
| Groom Cup Round Three Quarter Final | |||
| 03/28/2009 | Heyside FC | 10 - 3 | Fenay Bridge FC |
| 04/04/2009 | Heyside FC | 2 - 5 | Shelley |
| 04/09/2009 | Linthwaite Athletic | 2 - 10 | Heyside FC |
| 04/11/2009 | Heyside FC | 3 - 1 | Brook Motors |
| Groom Cup Semi Final | |||
| 04/13/2009 | Heyside FC | 1 - 0 | Grange Moor |
| 04/18/2009 | Heyside FC | 7 - 1 | Dalton Crusaders |
| 04/25/2009 | Dalton Crusaders | 3 - 6 | Heyside FC |
| 04/28/2009 | Upperthong | 2 - 4 | Heyside FC |
| Groom Cup Final | |||
| 05/01/2009 | Skelmanthorpe | 3 - 4 | Heyside FC |
| 05/05/2009 | Paddock Rangers | 0 - 2 | Heyside FC |
| 05/09/2009 | Heyside FC | 3 - 7 | Skelmanthorpe |