| Division One | |||
| 25/08/1999 | Kirkheaton Rovers | 4 - 2 | Storthes Hall |
| 01/09/1999 | Kirkheaton Rovers | 0 - 1 | Honley |
| 04/09/1999 | Britannia Sports | 4 - 2 | Kirkheaton Rovers |
| 11/09/1999 | Kirkheaton Rovers | 2 - 0 | Marsden |
| 18/09/1999 | Shepley | 2 - 0 | Kirkheaton Rovers |
| 25/09/1999 | Kirkheaton Rovers | 0 - 2 | Brackenhall Utd |
| West Riding Challenge Cup Preliminary Round | |||
| 09/10/1999 | Skipton Bulldogs | 3 - 2 | Kirkheaton Rovers |
| FA Challenge Cup Round One | |||
| 16/10/1999 | S.G.Singh Sabha | 0 - 7 | Kirkheaton Rovers |
| 23/10/1999 | Kirkheaton Rovers | 3 - 1 | Almondbury Utd |
| 30/10/1999 | Skelmanthorpe | 3 - 2 | Kirkheaton Rovers |
| Barlow Cup Round One | |||
| 13/11/1999 | Kirkheaton Rovers | 8 - 0 | Scholes |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Kirkheaton Rovers | 1 - 5 | Diggle |
| 27/11/1999 | Storthes Hall | 0 - 0 | Kirkheaton Rovers |
| 04/12/1999 | Kirkheaton Rovers | 2 - 2 | Wooldale Wanderers |
| 18/12/1999 | Kirkheaton Rovers | 0 - 2 | Kirkburton |
| Barlow Cup Round Two | |||
| 08/01/2000 | Berry Brow Lib | 3 - 3 | Kirkheaton Rovers |
| 15/01/2000 | Kirkheaton Rovers | 2 - 1 | Shepley |
| 29/01/2000 | Honley | 4 - 3 | Kirkheaton Rovers |
| 05/02/2000 | Kirkheaton Rovers | 0 - 4 | Britannia Sports |
| Barlow Cup Round Two | |||
| 12/02/2000 | Kirkheaton Rovers | 4 - 1 | Berry Brow Lib |
| 19/02/2000 | Heywood Sports | 3 - 2 | Kirkheaton Rovers |
| 26/02/2000 | Wooldale Wanderers | 7 - 1 | Kirkheaton Rovers |
| 04/03/2000 | Kirkburton | 3 - 0 | Kirkheaton Rovers |
| Barlow Cup Round Three Quarter Final | |||
| 11/03/2000 | Brackenhall Utd | 6 - 2 | Kirkheaton Rovers |
| 18/03/2000 | Marsden | 0 - 2 | Kirkheaton Rovers |
| 25/03/2000 | Kirkheaton Rovers | 0 - 4 | Skelmanthorpe |
| 01/04/2000 | Kirkheaton Rovers | 2 - 1 | Heywood Sports |
| 08/04/2000 | Almondbury Utd | 0 - 1 | Kirkheaton Rovers |
| 20/04/2000 | Brackenhall Utd | 2 - 1 | Kirkheaton Rovers |