| Reserve Division One | |||
| 25/08/1999 | Lindley Liberal | 3 - 4 | Kirkburton |
| 01/09/1999 | Kirkheaton Rovers | 5 - 1 | Kirkburton |
| 04/09/1999 | Kirkburton | 5 - 2 | Honley |
| 11/09/1999 | Shepley | 1 - 4 | Kirkburton |
| 25/09/1999 | Brackenhall Utd | 6 - 1 | Kirkburton |
| 02/10/1999 | Kirkburton | 6 - 3 | Berry Brow Lib |
| 09/10/1999 | Kirkburton | 4 - 1 | Uppermill Res |
| 16/10/1999 | Shelley | 0 - 3 | Kirkburton |
| 23/10/1999 | Slaithwaite Utd | 4 - 1 | Kirkburton |
| 30/10/1999 | Kirkburton | 10 - 2 | Shelley |
| 06/11/1999 | Heywood Sports | 2 - 3 | Kirkburton |
| Richardson Cup Round Two | |||
| 13/11/1999 | Kirkburton | 4 - 1 | Netherton |
| 20/11/1999 | Diggle | 1 - 3 | Kirkburton |
| 27/11/1999 | Kirkburton | 1 - 4 | Britannia Sports |
| 04/12/1999 | Honley | 0 - 1 | Kirkburton |
| 08/01/2000 | Almondbury Utd | 7 - 0 | Kirkburton |
| FA Junior Cup Round Two | |||
| 15/01/2000 | Kirkburton | 3 - 0 | Uppermill Res |
| 22/01/2000 | Kirkburton | 4 - 1 | Lindley Liberal |
| 29/01/2000 | Kirkburton | 3 - 0 | Kirkheaton Rovers |
| 12/02/2000 | Berry Brow Lib | 0 - 9 | Kirkburton |
| 19/02/2000 | Britannia Sports | 1 - 2 | Kirkburton |
| FA Junior Cup Round Three Quarter Finals | |||
| 26/02/2000 | Kirkburton | 6 - 0 | Weavers |
| Richardson Cup Round Three Quarter Final | |||
| 11/03/2000 | Kirkburton | 4 - 1 | Wooldale Wanderers |
| 18/03/2000 | Kirkburton | 4 - 0 | Slaithwaite Utd |
| 25/03/2000 | Kirkburton | 3 - 2 | Brackenhall Utd |
| FA Junior Cup Semi Final | |||
| 31/03/2000 | Kirkburton | 3 - 1 | Wooldale Wanderers |
| Richardson Cup Semi Final | |||
| 04/04/2000 | Kirkburton | P - P | Brackenhall Utd |
| 08/04/2000 | Uppermill Res | 3 - 1 | Kirkburton |
| 15/04/2000 | Kirkburton | 4 - 1 | Almondbury Utd |
| 22/04/2000 | Kirkburton | 2 - 0 | Heywood Sports |
| 25/04/2000 | Kirkburton | 0 - 3 | Shepley |
| FA Junior Cup Final | |||
| 28/04/2000 | Almondbury Utd | 2 - 0 | Kirkburton |
| 02/05/2000 | Kirkburton | 2 - 1 | Diggle |