| Division Four | |||
| 09/09/2000 | Netherthong | 6 - 0 | Cravens |
| 23/09/2000 | Brook Motors | 2 - 1 | Cravens |
| 30/09/2000 | Cravens | 4 - 5 | Deanhousemuir |
| 07/10/2000 | G.P.O. Sports | 1 - 1 | Cravens |
| FA Challenge Cup Round One | |||
| 21/10/2000 | Cravens | 2 - 4 | Woodman |
| 28/10/2000 | The Stag FC | 3 - 5 | Cravens |
| 18/11/2000 | Cravens | 5 - 1 | The Stag FC |
| 25/11/2000 | Moldgreen | 1 - 2 | Cravens |
| 02/12/2000 | Cravens | 1 - 1 | Scapegoat Hill Utd |
| 16/12/2000 | Cravens | 3 - 3 | Upperthong SC |
| Groom Cup Preliminary Round | |||
| 13/01/2001 | Oakes WMC | 4 - 5 | Cravens |
| 20/01/2001 | Cravens | 4 - 1 | Woodman |
| 27/01/2001 | Cravens | 2 - 0 | Brook Motors |
| Groom Cup Round One | |||
| 03/02/2001 | YMCA FC | 4 - 7 | Cravens |
| Groom Cup Round Two | |||
| 10/02/2001 | Lockwood | 4 - 3 | Cravens |
| 17/02/2001 | Lindley | 2 - 2 | Cravens |
| 24/02/2001 | Cravens | 3 - 2 | Moldgreen |
| 17/03/2001 | Cravens | 2 - 1 | Lindley |
| 31/03/2001 | Woodman | P - P | Cravens |
| 10/04/2001 | Upperthong SC | 2 - 1 | Cravens |
| 14/04/2001 | Deanhousemuir | 1 - 4 | Cravens |
| 17/04/2001 | Cravens | 0 - 1 | Holmbridge |
| 21/04/2001 | Cravens | 2 - 0 | G.P.O. Sports |
| 26/04/2001 | Holmbridge | 4 - 2 | Cravens |
| 01/05/2001 | Cravens | 0 - 0 | Netherthong |
| 01/05/2001 | Scapegoat Hill Utd | 0 - 0 | Cravens |