| Division Five | |||
| 09/09/2000 | Oakes WMC | 5 - 2 | YMCA FC |
| 23/09/2000 | Oakes WMC | 2 - 5 | Newsome WMC |
| 30/09/2000 | Feney Bridge FC | 3 - 4 | Oakes WMC |
| FA Challenge Cup Round One | |||
| 21/10/2000 | Oakes WMC | 2 - 4 | Sovereign Sports |
| 28/10/2000 | Woolpack St John | 0 - 5 | Oakes WMC |
| 18/11/2000 | Oakes WMC | 1 - 2 | Newsome WMC |
| 25/11/2000 | Oakes WMC | 0 - 2 | Paddock Rangers |
| 02/12/2000 | Feney Bridge FC | 2 - 0 | Oakes WMC |
| 16/12/2000 | Newsome WMC | 3 - 2 | Oakes WMC |
| 23/12/2000 | Oakes WMC | 1 - 4 | Feney Bridge FC |
| 06/01/2001 | Linthwaite Athletic | 3 - 3 | Oakes WMC |
| Groom Cup Preliminary Round | |||
| 13/01/2001 | Oakes WMC | 4 - 5 | Cravens |
| 27/01/2001 | Oakes WMC | 7 - 0 | Woolpack St John |
| 10/02/2001 | Oakes WMC | 1 - 5 | S.G.Singh Sabha |
| 17/02/2001 | YMCA FC | 3 - 7 | Oakes WMC |
| 24/02/2001 | Paddock Rangers | 1 - 2 | Oakes WMC |
| 10/03/2001 | Oakes WMC | 1 - 3 | Linthwaite Athletic |
| 17/03/2001 | Oakes WMC | 6 - 1 | Linthwaite Athletic |
| 24/03/2001 | S.G.Singh Sabha | 6 - 0 | Oakes WMC |
| 31/03/2001 | Oakes WMC | 3 - 5 | YMCA FC |
| 07/04/2001 | Paddock Rangers | 1 - 1 | Oakes WMC |
| 14/04/2001 | Woolpack St John | 4 - 0 | Oakes WMC |
| 21/04/2001 | S.G.Singh Sabha | P - P | Oakes WMC |