| Division Four | |||
| 04/09/1999 | Walkers Arms | 0 - 8 | Weavers |
| 18/09/1999 | Hade Edge | 2 - 5 | Weavers |
| 25/09/1999 | Weavers | 4 - 0 | Netherthong |
| 02/10/1999 | Scapegoat Hill Utd | 1 - 0 | Weavers |
| 09/10/1999 | Aimbry | 1 - 1 | Weavers |
| 23/10/1999 | Weavers | 2 - 2 | Upperthong SC |
| 30/10/1999 | The Stag FC | 4 - 3 | Weavers |
| 06/11/1999 | Holmbridge | 2 - 3 | Weavers |
| Groom Cup Round One | |||
| 13/11/1999 | Weavers | P - P | Thongsbridge Ath |
| FA Challenge Cup Round One | |||
| 20/11/1999 | Old Collegians (OBL) | 2 - 1 | Weavers |
| 27/11/1999 | G.P.O. Sports | 1 - 4 | Weavers |
| Groom Cup Round Two | |||
| 08/01/2000 | Little John | 1 - 2 | Weavers |
| 15/01/2000 | Weavers | 3 - 1 | Scapegoat Hill Utd |
| 22/01/2000 | Weavers | 4 - 1 | Walkers Arms |
| 12/02/2000 | Weavers | 11 - 0 | Woodman |
| 19/02/2000 | Weavers | 4 - 3 | G.P.O. Sports |
| 26/02/2000 | Weavers | 4 - 1 | Aimbry |
| 04/03/2000 | Upperthong SC | 1 - 0 | Weavers |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2000 | The Stag FC | 2 - 2 | Weavers |
| 18/03/2000 | Weavers | 2 - 3 | Hade Edge |
| Groom Cup Round Three Quarter Final | |||
| 25/03/2000 | Weavers | 4 - 1 | The Stag FC |
| 01/04/2000 | Woodman | 2 - 4 | Weavers |
| Groom Cup Semi Final | |||
| 06/04/2000 | Weavers | 1 - 0 | H.V.Academicals |
| 08/04/2000 | Netherthong | 2 - 3 | Weavers |
| 15/04/2000 | Weavers | 4 - 3 | The Stag FC |
| 22/04/2000 | Weavers | 5 - 1 | Holmbridge |
| Groom Cup Final | |||
| 25/04/2000 | Weavers | 1 - 1 | Cumberworth |