| Division One | |||
| 25/08/1999 | Kirkburton | 1 - 1 | Brackenhall Utd |
| 01/09/1999 | Brackenhall Utd | 3 - 2 | Heywood Sports |
| 04/09/1999 | Almondbury Utd | 1 - 2 | Brackenhall Utd |
| 11/09/1999 | Brackenhall Utd | 3 - 0 | Skelmanthorpe |
| 18/09/1999 | Marsden | 0 - 6 | Brackenhall Utd |
| 25/09/1999 | Kirkheaton Rovers | 0 - 2 | Brackenhall Utd |
| West Riding Challenge Cup Preliminary Round | |||
| 09/10/1999 | Littletown | 0 - 4 | Brackenhall Utd |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Moldgreen | 1 - 8 | Brackenhall Utd |
| 23/10/1999 | Brackenhall Utd | 5 - 1 | Marsden |
| 30/10/1999 | Shepley | 2 - 4 | Brackenhall Utd |
| West Riding Challenge Cup Round Two | |||
| 06/11/1999 | Golcar Utd | 1 - 0 | Brackenhall Utd |
| Barlow Cup Round One | |||
| 13/11/1999 | Brackenhall Utd | 3 - 1 | Hepworth Utd |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Brackenhall Utd | 6 - 2 | Almondburians (OBL) |
| 27/11/1999 | Skelmanthorpe | 1 - 1 | Brackenhall Utd |
| 08/01/2000 | Brackenhall Utd | 1 - 1 | Almondbury Utd |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Diggle | 1 - 3 | Brackenhall Utd |
| 05/02/2000 | Wooldale Wanderers | 3 - 0 | Brackenhall Utd |
| Barlow Cup Round Two | |||
| 12/02/2000 | Scissett | 2 - 6 | Brackenhall Utd |
| FA Challenge Cup Round Four Quarter Final | |||
| 19/02/2000 | Brackenhall Utd | 0 - 0 | Storthes Hall (WR) |
| 26/02/2000 | Brackenhall Utd | 6 - 3 | Shepley |
| 04/03/2000 | Honley | 1 - 2 | Brackenhall Utd |
| Barlow Cup Round Three Quarter Final | |||
| 11/03/2000 | Brackenhall Utd | 6 - 2 | Kirkheaton Rovers |
| FA Challenge Cup Round Four Quarter Final | |||
| 18/03/2000 | Storthes Hall (WR) | 3 - 1 | Brackenhall Utd |
| 25/03/2000 | Brackenhall Utd | 2 - 1 | Britannia Sports |
| 01/04/2000 | Brackenhall Utd | 5 - 0 | Storthes Hall |
| 06/04/2000 | Brackenhall Utd | 3 - 0 | Kirkburton |
| 08/04/2000 | Britannia Sports | 0 - 0 | Brackenhall Utd |
| 11/04/2000 | Heywood Sports | 0 - 2 | Brackenhall Utd |
| 15/04/2000 | Brackenhall Utd | 3 - 0 | Honley |
| 20/04/2000 | Brackenhall Utd | 2 - 1 | Kirkheaton Rovers |
| Barlow Cup Semi Final | |||
| 24/04/2000 | Wooldale Wanderers | P - P | Brackenhall Utd |
| 06/05/2000 | Brackenhall Utd | 7 - 0 | Wooldale Wanderers |
| 11/05/2000 | Storthes Hall | 1 - 3 | Brackenhall Utd |