| Division Five | |||
| 09/09/2000 | S.G.Singh Sabha | 2 - 0 | Woolpack St John |
| 23/09/2000 | Woolpack St John | 1 - 6 | Feney Bridge FC |
| 30/09/2000 | YMCA FC | 3 - 5 | Woolpack St John |
| 07/10/2000 | Woolpack St John | 3 - 1 | Linthwaite Athletic |
| 14/10/2000 | Newsome WMC | 4 - 0 | Woolpack St John |
| 28/10/2000 | Woolpack St John | 0 - 5 | Oakes WMC |
| FA Challenge Cup Round One | |||
| 18/11/2000 | Deanhousemuir | 2 - 0 | Woolpack St John |
| 02/12/2000 | YMCA FC | 3 - 1 | Woolpack St John |
| 16/12/2000 | Woolpack St John | 1 - 2 | Paddock Rangers |
| 23/12/2000 | Woolpack St John | 1 - 2 | YMCA FC |
| 06/01/2001 | Woolpack St John | 1 - 6 | Newsome WMC |
| Groom Cup Round One | |||
| 13/01/2001 | Upperthong SC | 4 - 1 | Woolpack St John |
| 20/01/2001 | Woolpack St John | 2 - 3 | S.G.Singh Sabha |
| 27/01/2001 | Oakes WMC | 7 - 0 | Woolpack St John |
| 03/02/2001 | S.G.Singh Sabha | 5 - 1 | Woolpack St John |
| 17/02/2001 | Woolpack St John | 1 - 1 | Feney Bridge FC |
| 24/02/2001 | Feney Bridge FC | 7 - 0 | Woolpack St John |
| 10/03/2001 | Newsome WMC | 6 - 1 | Woolpack St John |
| 17/03/2001 | Woolpack St John | 2 - 3 | Paddock Rangers |
| 24/03/2001 | Woolpack St John | P - P | Linthwaite Athletic |
| 31/03/2001 | Paddock Rangers | 2 - 2 | Woolpack St John |
| 10/04/2001 | Linthwaite Athletic | 4 - 1 | Woolpack St John |
| 14/04/2001 | Woolpack St John | 4 - 0 | Oakes WMC |