| Division Four | |||
| 04/09/1999 | The Stag FC | 1 - 0 | Netherthong |
| 11/09/1999 | Scapegoat Hill Utd | 5 - 0 | The Stag FC |
| 18/09/1999 | The Stag FC | 2 - 4 | Aimbry |
| 25/09/1999 | Upperthong SC | 0 - 4 | The Stag FC |
| 02/10/1999 | The Stag FC | 4 - 2 | Woodman |
| 09/10/1999 | The Stag FC | 4 - 2 | G.P.O. Sports |
| FA Challenge Cup Round One | |||
| 16/10/1999 | The Stag FC | 0 - 3 | Aimbry |
| 23/10/1999 | Holmbridge | 2 - 2 | The Stag FC |
| 30/10/1999 | The Stag FC | 4 - 3 | Weavers |
| 06/11/1999 | Walkers Arms | 1 - 2 | The Stag FC |
| Groom Cup Round One | |||
| 13/11/1999 | The Stag FC | 5 - 5 | Paddock Rangers |
| 27/11/1999 | The Stag FC | 2 - 3 | Walkers Arms |
| 04/12/1999 | The Stag FC | 5 - 0 | Hade Edge |
| 18/12/1999 | The Stag FC | 2 - 3 | Upperthong SC |
| 08/01/2000 | Aimbry | 1 - 2 | The Stag FC |
| Groom Cup Round One | |||
| 15/01/2000 | Paddock Rangers | 0 - 2 | The Stag FC |
| 22/01/2000 | Netherthong | 2 - 6 | The Stag FC |
| 29/01/2000 | The Stag FC | 2 - 5 | Scapegoat Hill Utd |
| Groom Cup Round Two | |||
| 12/02/2000 | The Stag FC | 2 - 0 | Cartworth Moor |
| 19/02/2000 | Woodman | 1 - 1 | The Stag FC |
| 26/02/2000 | G.P.O. Sports | 1 - 3 | The Stag FC |
| 04/03/2000 | The Stag FC | 1 - 1 | Holmbridge |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2000 | The Stag FC | 2 - 2 | Weavers |
| Groom Cup Round Three Quarter Final | |||
| 25/03/2000 | Weavers | 4 - 1 | The Stag FC |
| 01/04/2000 | Hade Edge | 2 - 0 | The Stag FC |
| 15/04/2000 | Weavers | 4 - 3 | The Stag FC |