| Division Two | |||
| 09/13/2008 | Netherton | 1 - 1 | Westend |
| 09/20/2008 | Westend | 4 - 4 | Lamb Inn FC |
| 09/27/2008 | Cumberworth | 0 - 1 | Westend |
| 10/04/2008 | Westend | 0 - 4 | Berry Brow Lib |
| 10/11/2008 | Mount | 2 - 1 | Westend |
| FA Challenge Cup Round One | |||
| 10/18/2008 | Collegians (OBL) | 4 - 3 | Westend |
| 10/25/2008 | Westend | 3 - 3 | Slaithwaite Utd |
| Barlow Cup Round One | |||
| 11/08/2008 | Netherton | 5 - 1 | Westend |
| 11/22/2008 | KKS Ashbrow | 4 - 1 | Westend |
| 11/29/2008 | Westend | 2 - 2 | Stag FC |
| 12/20/2008 | Honley | 0 - 2 | Westend |
| 01/24/2009 | Scholes | 0 - 2 | Westend |
| 01/31/2009 | Westend | 1 - 1 | Netherton |
| 02/21/2009 | Westend | 3 - 0 | Mount |
| 02/28/2009 | Westend | 1 - 3 | Cumberworth |
| 03/07/2009 | Kirkheaton Rovers | 1 - 2 | Westend |
| 03/14/2009 | Westend | 1 - 2 | Honley |
| 03/21/2009 | Lamb Inn FC | 2 - 1 | Westend |
| 03/28/2009 | Westend | 1 - 1 | Scholes |
| 04/04/2009 | Slaithwaite Utd | 1 - 1 | Westend |
| 04/07/2009 | Berry Brow Lib | 0 - 1 | Westend |
| 04/11/2009 | Westend | 2 - 0 | KKS Ashbrow |
| 04/18/2009 | Stag FC | 1 - 4 | Westend |
| 04/25/2009 | Moldgreen | 3 - 1 | Westend |
| 04/28/2009 | Westend | 3 - 2 | Kirkheaton Rovers |
| 05/02/2009 | Westend | 1 - 5 | Moldgreen |