| Division Two | |||
| 09/13/2008 | Kirkheaton Rovers | 4 - 3 | Stag FC |
| 09/20/2008 | Kirkheaton Rovers | 0 - 3 | Berry Brow Lib |
| 09/27/2008 | Kirkheaton Rovers | 1 - 4 | Honley |
| West Riding Challenge Trophy Round One | |||
| 10/04/2008 | Kirkheaton Rovers | 3 - 2 | Ripon City |
| 10/18/2008 | Cumberworth | 1 - 1 | Kirkheaton Rovers |
| 10/25/2008 | Kirkheaton Rovers | 0 - 3 | Netherton |
| West Riding Challenge Trophy Round Two | |||
| 11/01/2008 | Kirkheaton Rovers | 6 - 1 | Swillinagton Saints |
| Barlow Cup Round One | |||
| 11/08/2008 | Slaithwaite Utd | 2 - 3 | Kirkheaton Rovers |
| FA Challenge Cup Round Two | |||
| 11/15/2008 | Kirkheaton Rovers | 0 - 3 | Storthes Hall (WR) |
| 11/22/2008 | Kirkheaton Rovers | 2 - 1 | Cumberworth |
| 11/29/2008 | Mount | 0 - 3 | Kirkheaton Rovers |
| West Riding Challenge Trophy Round Three | |||
| 12/06/2008 | Fairburn Utd | 1 - 6 | Kirkheaton Rovers |
| Barlow Cup Round Two | |||
| 12/13/2008 | Heywoods Irish Centre FC | 1 - 0 | Kirkheaton Rovers |
| 12/20/2008 | Berry Brow Lib | 1 - 3 | Kirkheaton Rovers |
| West Riding Challenge Trophy Round Four | |||
| 01/17/2009 | Knaresborough Town | 1 - 3 | Kirkheaton Rovers |
| 01/24/2009 | KKS Ashbrow | 1 - 3 | Kirkheaton Rovers |
| 01/31/2009 | Stag FC | 1 - 6 | Kirkheaton Rovers |
| Wesr Riding County FA Challenge Trophy QF | |||
| 02/21/2009 | Kirkheaton Rovers | 1 - 5 | Storthes Hall (WR) |
| 02/28/2009 | Lamb Inn FC | 5 - 3 | Kirkheaton Rovers |
| 03/07/2009 | Kirkheaton Rovers | 1 - 2 | Westend |
| 03/14/2009 | Slaithwaite Utd | 3 - 1 | Kirkheaton Rovers |
| 03/21/2009 | Kirkheaton Rovers | 0 - 6 | Moldgreen |
| 04/04/2009 | Netherton | 3 - 2 | Kirkheaton Rovers |
| 04/07/2009 | Moldgreen | 2 - 1 | Kirkheaton Rovers |
| 04/11/2009 | Kirkheaton Rovers | 0 - 3 | Slaithwaite Utd |
| 04/14/2009 | Kirkheaton Rovers | 2 - 1 | KKS Ashbrow |
| 04/16/2009 | Honley | 0 - 4 | Kirkheaton Rovers |
| 04/18/2009 | Kirkheaton Rovers | 5 - 0 | Mount |
| 04/21/2009 | Kirkheaton Rovers | 1 - 1 | Lamb Inn FC |
| 04/25/2009 | Scholes | 2 - 6 | Kirkheaton Rovers |
| 04/28/2009 | Westend | 3 - 2 | Kirkheaton Rovers |
| 05/02/2009 | Kirkheaton Rovers | 6 - 2 | Scholes |