| Division One | |||
| 25/08/1999 | Britannia Sports | 0 - 2 | Skelmanthorpe |
| 01/09/1999 | Wooldale Wanderers | 6 - 0 | Britannia Sports |
| 04/09/1999 | Britannia Sports | 4 - 2 | Kirkheaton Rovers |
| 11/09/1999 | Honley | 1 - 5 | Britannia Sports |
| 18/09/1999 | Britannia Sports | 4 - 4 | Storthes Hall |
| 25/09/1999 | Britannia Sports | 9 - 1 | Marsden |
| West Riding Challenge Cup Preliminary Round | |||
| 02/10/1999 | Britannia Sports | 2 - 0 | Silsden |
| 09/10/1999 | Britannia Sports | 4 - 4 | Kirkburton |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Shepley | 3 - 1 | Britannia Sports |
| 23/10/1999 | Kirkburton | 2 - 1 | Britannia Sports |
| 30/10/1999 | Britannia Sports | 5 - 0 | Honley |
| West Riding Challenge Cup Round Two | |||
| 06/11/1999 | Britannia Sports | 5 - 1 | Batley WMC |
| Barlow Cup Round One | |||
| 13/11/1999 | Britannia Sports | 2 - 4 | Kirkburton |
| 27/11/1999 | Britannia Sports | 3 - 1 | Heywood Sports |
| West Riding Challenge Cup Round Three | |||
| 18/12/1999 | Ardsley Celtic | 2 - 0 | Britannia Sports |
| 15/01/2000 | Britannia Sports | 1 - 2 | Wooldale Wanderers |
| 22/01/2000 | Heywood Sports | 2 - 3 | Britannia Sports |
| 05/02/2000 | Kirkheaton Rovers | 0 - 4 | Britannia Sports |
| 12/02/2000 | Almondbury Utd | 1 - 1 | Britannia Sports |
| 19/02/2000 | Storthes Hall | 0 - 3 | Britannia Sports |
| 04/03/2000 | Marsden | 2 - 2 | Britannia Sports |
| 11/03/2000 | Britannia Sports | 4 - 1 | Almondbury Utd |
| 18/03/2000 | Shepley | 1 - 1 | Britannia Sports |
| 25/03/2000 | Brackenhall Utd | 2 - 1 | Britannia Sports |
| 08/04/2000 | Britannia Sports | 0 - 0 | Brackenhall Utd |
| 22/04/2000 | Britannia Sports | 1 - 2 | Shepley |
| 29/04/2000 | Skelmanthorpe | 1 - 2 | Britannia Sports |