| Reserve Division Three | |||
| 25/08/1999 | Cartworth Moor | 4 - 7 | Upperthong SC |
| 01/09/1999 | Upperthong SC | 7 - 1 | Netherthong |
| 04/09/1999 | Little John | 1 - 8 | Upperthong SC |
| 11/09/1999 | Upperthong SC | 5 - 0 | Flockton FC |
| 25/09/1999 | Lepton Highlanders | 7 - 4 | Upperthong SC |
| 09/10/1999 | Lindley | 3 - 3 | Upperthong SC |
| 16/10/1999 | Upperthong SC | 7 - 5 | Little John |
| 23/10/1999 | Upperthong SC | 12 - 0 | Holmbridge |
| 30/10/1999 | Upperthong SC | 1 - 1 | Linthwaite Athletic |
| 06/11/1999 | Upperthong SC | 2 - 3 | Cumberworth |
| Gee Cup Round One | |||
| 13/11/1999 | Upperthong SC | 4 - 0 | Cravens |
| 20/11/1999 | Holmbridge | 2 - 12 | Upperthong SC |
| 27/11/1999 | Weavers | 1 - 3 | Upperthong SC |
| 08/01/2000 | Meltham Athletic | 1 - 1 | Upperthong SC |
| 15/01/2000 | Linthwaite Athletic | 0 - 1 | Upperthong SC |
| Gee Cup Round Two | |||
| 22/01/2000 | Cumberworth | 0 - 2 | Upperthong SC |
| 05/02/2000 | Cumberworth | 2 - 2 | Upperthong SC |
| 12/02/2000 | Upperthong SC | 3 - 2 | Meltham Athletic |
| 19/02/2000 | Upperthong SC | 5 - 2 | Mount |
| 26/02/2000 | Upperthong SC | 3 - 3 | Lindley |
| Gee Cup Round Three Quarter Final | |||
| 11/03/2000 | Upperthong SC | 4 - 1 | Lindley |
| 18/03/2000 | Upperthong SC | 6 - 1 | Cartworth Moor |
| 25/03/2000 | Upperthong SC | 5 - 1 | Weavers |
| 01/04/2000 | Mount | 0 - 6 | Upperthong SC |
| 08/04/2000 | Upperthong SC | 5 - 0 | Lepton Highlanders |
| Gee Cup Semi Final | |||
| 11/04/2000 | Upperthong SC | 2 - 3 | Marsden 'A' |
| 15/04/2000 | Flockton FC | 1 - 3 | Upperthong SC |
| 18/04/2000 | Netherthong | 3 - 2 | Upperthong SC |