| Division Two | |||
| 09/20/2008 | KKS Ashbrow | 3 - 4 | Netherton |
| 09/27/2008 | Lamb Inn FC | 6 - 1 | KKS Ashbrow |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Britannia Sports Res | 2 - 4 | KKS Ashbrow |
| 10/11/2008 | Stag FC | 1 - 4 | KKS Ashbrow |
| 10/25/2008 | KKS Ashbrow | 2 - 2 | Scholes |
| West Riding Challenge Trophy Round Two | |||
| 11/01/2008 | Campion | 1 - 2 | KKS Ashbrow |
| Barlow Cup Round One | |||
| 11/08/2008 | KKS Ashbrow | P - P | Moldgreen |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | KKS Ashbrow | 4 - 2 | Dalton Crusaders |
| 11/22/2008 | KKS Ashbrow | 4 - 1 | Westend |
| 11/29/2008 | Moldgreen | 0 - 3 | KKS Ashbrow |
| West Riding Challenge Trophy Round Three | |||
| 12/06/2008 | KKS Ashbrow | 4 - 0 | Volunteer Arms |
| FA Challenge Cup Round Three | |||
| 12/20/2008 | Lepton Highlanders | 5 - 4 | KKS Ashbrow |
| West Riding Challenge Trophy Round Four | |||
| 01/03/2009 | KKS Ashbrow | 2 - 3 | Lamb Inn FC |
| 01/17/2009 | KKS Ashbrow | 3 - 0 | Honley |
| 01/24/2009 | KKS Ashbrow | 1 - 3 | Kirkheaton Rovers |
| Wesr Riding County FA Challenge Trophy QF | |||
| 02/21/2009 | Otley Town | 0 - 1 | KKS Ashbrow |
| 02/28/2009 | KKS Ashbrow | 4 - 3 | Moldgreen |
| 03/07/2009 | Mount | 1 - 1 | KKS Ashbrow |
| 03/14/2009 | Berry Brow Lib | 4 - 2 | KKS Ashbrow |
| 03/21/2009 | KKS Ashbrow | 0 - 2 | Slaithwaite Utd |
| 03/28/2009 | KKS Ashbrow | 3 - 0 | Mount |
| 04/04/2009 | Cumberworth | 1 - 0 | KKS Ashbrow |
| 04/09/2009 | Scholes | 3 - 0 | KKS Ashbrow |
| 04/11/2009 | Westend | 2 - 0 | KKS Ashbrow |
| 04/14/2009 | Kirkheaton Rovers | 2 - 1 | KKS Ashbrow |
| 04/16/2009 | KKS Ashbrow | 0 - 5 | Lamb Inn FC |
| 04/18/2009 | KKS Ashbrow | 2 - 3 | Cumberworth |
| 04/23/2009 | KKS Ashbrow | 1 - 0 | Berry Brow Lib |
| 04/25/2009 | Slaithwaite Utd | 1 - 2 | KKS Ashbrow |
| 04/28/2009 | Honley | 0 - 1 | KKS Ashbrow |
| 05/02/2009 | KKS Ashbrow | 8 - 1 | Stag FC |
| 05/05/2009 | Netherton | 4 - 2 | KKS Ashbrow |