| Division Three | |||
| 25/08/1999 | Uppermill | 1 - 1 | Little John |
| 01/09/1999 | Uppermill | 3 - 3 | New Mill 94 |
| 04/09/1999 | Cumberworth | 2 - 1 | Uppermill |
| 11/09/1999 | Uppermill | 3 - 0 | Black Star |
| 18/09/1999 | Netherton | 1 - 0 | Uppermill |
| 25/09/1999 | Uppermill | 6 - 0 | Lindley |
| 02/10/1999 | KKS Ashbrow | 2 - 2 | Uppermill |
| 09/10/1999 | Uppermill | 0 - 1 | Golcar Utd |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Uppermill | 1 - 3 | Storthes Hall (WR) |
| 23/10/1999 | Uppermill | 3 - 4 | Flockton FC |
| 30/10/1999 | H.V.Academicals | 1 - 2 | Uppermill |
| 06/11/1999 | Uppermill | 3 - 2 | Cravens |
| Groom Cup Round One | |||
| 13/11/1999 | Uppermill | 3 - 1 | S.G.Singh Sabha |
| 20/11/1999 | Golcar Utd | 0 - 2 | Uppermill |
| 27/11/1999 | Cartworth Moor | 0 - 0 | Uppermill |
| Groom Cup Round Two | |||
| 15/01/2000 | Hade Edge | 1 - 3 | Uppermill |
| 22/01/2000 | Uppermill | 4 - 3 | Netherton |
| 05/02/2000 | Uppermill | 8 - 0 | Cartworth Moor |
| 12/02/2000 | Cravens | 0 - 5 | Uppermill |
| 19/02/2000 | Uppermill | 3 - 4 | KKS Ashbrow |
| 26/02/2000 | Lindley | 1 - 3 | Uppermill |
| 04/03/2000 | Uppermill | 4 - 1 | H.V.Academicals |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2000 | Uppermill | 0 - 0 | H.V.Academicals |
| 18/03/2000 | Flockton FC | 1 - 3 | Uppermill |
| Groom Cup Round Three Quarter Final | |||
| 25/03/2000 | H.V.Academicals | 2 - 1 | Uppermill |
| 01/04/2000 | New Mill 94 | 1 - 2 | Uppermill |
| 08/04/2000 | Little John | 2 - 5 | Uppermill |
| 15/04/2000 | Uppermill | 3 - 0 | Cumberworth |
| 22/04/2000 | Black Star | 3 - 1 | Uppermill |