| Division Four | |||
| 04/09/1999 | Upperthong SC | 1 - 1 | Scapegoat Hill Utd |
| 11/09/1999 | Aimbry | 3 - 2 | Upperthong SC |
| 18/09/1999 | Upperthong SC | 1 - 3 | Walkers Arms |
| 25/09/1999 | Upperthong SC | 0 - 4 | The Stag FC |
| 02/10/1999 | G.P.O. Sports | 3 - 0 | Upperthong SC |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Upperthong SC | 0 - 5 | Houghton Main FC |
| 16/10/1999 | Woodman | 4 - 1 | Upperthong SC |
| 23/10/1999 | Weavers | 2 - 2 | Upperthong SC |
| 30/10/1999 | Walkers Arms | 8 - 2 | Upperthong SC |
| 06/11/1999 | Hade Edge | 2 - 2 | Upperthong SC |
| Groom Cup Preliminary Round | |||
| 13/11/1999 | KKS Ashbrow | 3 - 2 | Upperthong SC |
| 20/11/1999 | Upperthong SC | 1 - 0 | Hade Edge |
| 18/12/1999 | The Stag FC | 2 - 3 | Upperthong SC |
| 08/01/2000 | Upperthong SC | 3 - 1 | Netherthong |
| 15/01/2000 | Upperthong SC | 6 - 1 | Woodman |
| 22/01/2000 | Scapegoat Hill Utd | 1 - 3 | Upperthong SC |
| 05/02/2000 | Upperthong SC | 0 - 2 | G.P.O. Sports |
| 26/02/2000 | Holmbridge | 2 - 2 | Upperthong SC |
| 04/03/2000 | Upperthong SC | 1 - 0 | Weavers |
| 11/03/2000 | Netherthong | 2 - 0 | Upperthong SC |
| 19/03/2000 | Upperthong SC | P - P | Aimbry |
| 27/04/2000 | Upperthong SC | 4 - 2 | Holmbridge |