| Division One | |||
| 09/13/2008 | Hepworth Utd | 2 - 3 | Lepton Highlanders |
| 09/20/2008 | Lepton Highlanders | 4 - 2 | Britannia Sports |
| 09/27/2008 | Diggle | 1 - 1 | Lepton Highlanders |
| West Riding Challenge Cup Round One | |||
| 10/04/2008 | Golcar Utd (WR) | 2 - 1 | Lepton Highlanders |
| 10/11/2008 | Meltham Athletic | 0 - 1 | Lepton Highlanders |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Heyside FC | 2 - 3 | Lepton Highlanders |
| 10/25/2008 | Newsome WMC | 2 - 3 | Lepton Highlanders |
| 11/01/2008 | Lepton Highlanders | 4 - 1 | Wooldale Wanderers |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | Lamb Inn FC | 1 - 2 | Lepton Highlanders |
| 11/22/2008 | Wooldale Wanderers | 1 - 2 | Lepton Highlanders |
| 11/29/2008 | Lepton Highlanders | 2 - 0 | Shepley |
| 12/06/2008 | New Mill 94 | 0 - 4 | Lepton Highlanders |
| FA Challenge Cup Round Three | |||
| 12/20/2008 | Lepton Highlanders | 5 - 4 | KKS Ashbrow |
| 01/03/2009 | Lepton Highlanders | 3 - 2 | Hepworth Utd |
| 01/17/2009 | Shepley | 1 - 2 | Lepton Highlanders |
| Barlow Cup Round One | |||
| 01/24/2009 | Lepton Highlanders | 2 - 3 | Newsome WMC |
| FA Challenge Cup Round Four Quarter Final | |||
| 02/21/2009 | Netherton | 0 - 2 | Lepton Highlanders |
| 02/28/2009 | Lepton Highlanders | 3 - 1 | Uppermill |
| 03/07/2009 | Lepton Highlanders | 3 - 2 | New Mill 94 |
| 03/21/2009 | Lepton Highlanders | 4 - 2 | Diggle |
| 03/28/2009 | Uppermill | 2 - 3 | Lepton Highlanders |
| 04/04/2009 | Lepton Highlanders | 1 - 3 | Newsome WMC |
| FA Challenge Cup Semi Final | |||
| 04/11/2009 | Storthes Hall (WR) | 3 - 1 | Lepton Highlanders |
| 04/18/2009 | Lepton Highlanders | 3 - 4 | Heywood Irish Centre FC |
| 04/21/2009 | Britannia Sports | 4 - 2 | Lepton Highlanders |
| 04/25/2009 | Heywood Irish Centre FC | 1 - 7 | Lepton Highlanders |
| 05/02/2009 | Lepton Highlanders | 3 - 0 | Meltham Athletic |