| Division Four | |||
| 04/09/1999 | Aimbry | 2 - 0 | Woodman |
| 11/09/1999 | Woodman | 2 - 4 | Walkers Arms |
| FA Challenge Cup Preliminary Round | |||
| 18/09/1999 | Diggle | P - P | Woodman |
| 02/10/1999 | The Stag FC | 4 - 2 | Woodman |
| 16/10/1999 | Woodman | 4 - 1 | Upperthong SC |
| 23/10/1999 | Woodman | 1 - 2 | G.P.O. Sports |
| 30/10/1999 | Woodman | 1 - 1 | Netherthong |
| 06/11/1999 | Woodman | 3 - 2 | Scapegoat Hill Utd |
| Groom Cup Preliminary Round | |||
| 13/11/1999 | Oakes | 2 - 3 | Woodman |
| 27/11/1999 | Woodman | 0 - 4 | Holmbridge |
| Groom Cup Round One | |||
| 08/01/2000 | Woodman | 1 - 2 | Holmbridge |
| 15/01/2000 | Upperthong SC | 6 - 1 | Woodman |
| 22/01/2000 | Woodman | 2 - 2 | Aimbry |
| 05/02/2000 | Scapegoat Hill Utd | 4 - 3 | Woodman |
| 12/02/2000 | Weavers | 11 - 0 | Woodman |
| 19/02/2000 | Woodman | 1 - 1 | The Stag FC |
| 26/02/2000 | Hade Edge | 4 - 2 | Woodman |
| 04/03/2000 | G.P.O. Sports | 1 - 2 | Woodman |
| 11/03/2000 | Woodman | 1 - 5 | Hade Edge |
| 18/03/2000 | Netherthong | 3 - 1 | Woodman |
| 25/03/2000 | Walkers Arms | 2 - 4 | Woodman |
| 01/04/2000 | Woodman | 2 - 4 | Weavers |
| 15/04/2000 | Holmbridge | 5 - 0 | Woodman |