| Reserve Division One | |||
| 25/08/1999 | Brackenhall Utd | 3 - 1 | Slaithwaite Utd |
| 01/09/1999 | Heywood Sports | 2 - 3 | Brackenhall Utd |
| 04/09/1999 | Brackenhall Utd | 2 - 1 | Almondbury Utd |
| 11/09/1999 | Kirkheaton Rovers | 0 - 12 | Brackenhall Utd |
| 18/09/1999 | Brackenhall Utd | 6 - 2 | Shepley |
| 25/09/1999 | Brackenhall Utd | 6 - 1 | Kirkburton |
| 02/10/1999 | Uppermill Res | 1 - 3 | Brackenhall Utd |
| 09/10/1999 | Brackenhall Utd | 3 - 0 | Shelley |
| 16/10/1999 | Brackenhall Utd | 3 - 0 | Berry Brow Lib |
| 23/10/1999 | Britannia Sports | 3 - 3 | Brackenhall Utd |
| 30/10/1999 | Brackenhall Utd | 5 - 1 | Lindley Liberal |
| 06/11/1999 | Honley | 1 - 3 | Brackenhall Utd |
| 13/11/1999 | Shelley | 0 - 2 | Brackenhall Utd |
| 27/11/1999 | Brackenhall Utd | 2 - 0 | Diggle |
| 04/12/1999 | Lindley Liberal | 1 - 3 | Brackenhall Utd |
| Richardson Cup Round Two | |||
| 08/01/2000 | Diggle A | 2 - 4 | Brackenhall Utd |
| 15/01/2000 | Brackenhall Utd | 0 - 0 | Britannia Sports |
| 22/01/2000 | Slaithwaite Utd | 0 - 1 | Brackenhall Utd |
| 05/02/2000 | Brackenhall Utd | 2 - 1 | Heywood Sports |
| Richardson Cup Round Three Quarter Final | |||
| 12/02/2000 | New Mill 94 | 1 - 2 | Brackenhall Utd |
| 26/02/2000 | Berry Brow Lib | P - P | Brackenhall Utd |
| 04/03/2000 | Brackenhall Utd | 2 - 1 | Honley |
| 11/03/2000 | Shepley | 2 - 0 | Brackenhall Utd |
| 18/03/2000 | Brackenhall Utd | 5 - 0 | Kirkheaton Rovers |
| 25/03/2000 | Kirkburton | 3 - 2 | Brackenhall Utd |
| 01/04/2000 | Diggle | 5 - 4 | Brackenhall Utd |
| Richardson Cup Semi Final | |||
| 04/04/2000 | Kirkburton | P - P | Brackenhall Utd |
| 13/04/2000 | Brackenhall Utd | 0 - 0 | Uppermill Res |
| Richardson Cup Final | |||
| 18/04/2000 | Almondbury Utd | 2 - 0 | Brackenhall Utd |
| 20/04/2000 | Almondbury Utd | 1 - 1 | Brackenhall Utd |