| Division Five | |||
| 25/08/1999 | Laund Hill YMCA | 4 - 2 | Woolpack St John |
| 01/09/1999 | Woolpack St John | 1 - 1 | Deanhousemuir |
| 04/09/1999 | Woolpack St John | 0 - 3 | S.G.Singh Sabha |
| 11/09/1999 | Paddock Rangers | 2 - 3 | Woolpack St John |
| 18/09/1999 | Woolpack St John | 4 - 8 | Moldgreen |
| 25/09/1999 | Thongsbridge Ath | 3 - 5 | Woolpack St John |
| 02/10/1999 | Woolpack St John | 7 - 1 | Oakes |
| 09/10/1999 | Linthwaite Athletic | 8 - 0 | Woolpack St John |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Kirkburton | 5 - 1 | Woolpack St John |
| 23/10/1999 | Woolpack St John | 1 - 2 | Brook Motors |
| 30/10/1999 | Woolpack St John | 2 - 2 | Laund Hill YMCA |
| 06/11/1999 | Deanhousemuir | 1 - 0 | Woolpack St John |
| Groom Cup Round One | |||
| 13/11/1999 | Woolpack St John | 1 - 2 | Laund Hill YMCA |
| 20/11/1999 | Woolpack St John | 0 - 2 | Moldgreen |
| 27/11/1999 | Woolpack St John | 2 - 1 | S.G.Singh Sabha |
| 18/12/1999 | Woolpack St John | 1 - 3 | Thongsbridge Ath |
| 08/01/2000 | Paddock Rangers | 1 - 2 | Woolpack St John |
| 15/01/2000 | Woolpack St John | 0 - 5 | Brook Motors |
| 22/01/2000 | Oakes | 1 - 1 | Woolpack St John |
| 05/02/2000 | Brook Motors | 4 - 0 | Woolpack St John |
| 12/02/2000 | Moldgreen | 5 - 1 | Woolpack St John |
| 19/02/2000 | Woolpack St John | 1 - 6 | Linthwaite Athletic |
| 26/02/2000 | Woolpack St John | 3 - 5 | Oakes |
| 04/03/2000 | Thongsbridge Ath | 9 - 0 | Woolpack St John |
| 11/03/2000 | Laund Hill YMCA | 2 - 0 | Woolpack St John |
| 18/03/2000 | Woolpack St John | 2 - 7 | Deanhousemuir |
| 25/03/2000 | S.G.Singh Sabha | 3 - 3 | Woolpack St John |
| 01/04/2000 | Linthwaite Athletic | 12 - 1 | Woolpack St John |
| 08/04/2000 | Woolpack St John | 1 - 3 | Paddock Rangers |