| Division Three | |||
| 25/08/1999 | New Mill 94 | 4 - 2 | Golcar Utd |
| 01/09/1999 | Uppermill | 3 - 3 | New Mill 94 |
| 04/09/1999 | New Mill 94 | 7 - 0 | Flockton FC |
| 11/09/1999 | Cumberworth | 2 - 2 | New Mill 94 |
| 18/09/1999 | New Mill 94 | 4 - 2 | Little John |
| 25/09/1999 | Black Star | 2 - 2 | New Mill 94 |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | New Mill 94 | 7 - 2 | Cumberworth |
| 16/10/1999 | New Mill 94 | 6 - 0 | Lindley |
| 23/10/1999 | Cartworth Moor | 0 - 4 | New Mill 94 |
| Sheffield Junior Trophy Round Three | |||
| 13/11/1999 | Flockton FC | 3 - 5 | New Mill 94 |
| 20/11/1999 | New Mill 94 | 0 - 0 | H.V.Academicals |
| 27/11/1999 | New Mill 94 | 3 - 1 | KKS Ashbrow |
| 04/12/1999 | Little John | 0 - 1 | New Mill 94 |
| Sheffield Junior Trophy Round Five | |||
| 08/01/2000 | New Mill 94 | 0 - 1 | Hemsworth St Patricks |
| Groom Cup Round One | |||
| 15/01/2000 | New Mill 94 | 1 - 3 | Golcar Utd |
| 22/01/2000 | New Mill 94 | 2 - 1 | Cumberworth |
| 05/02/2000 | Flockton FC | 3 - 1 | New Mill 94 |
| 26/02/2000 | New Mill 94 | 4 - 2 | Black Star |
| 04/03/2000 | Cravens | 2 - 2 | New Mill 94 |
| 11/03/2000 | New Mill 94 | 2 - 0 | Cravens |
| 18/03/2000 | New Mill 94 | 4 - 0 | Cartworth Moor |
| 25/03/2000 | KKS Ashbrow | 1 - 3 | New Mill 94 |
| 01/04/2000 | New Mill 94 | 1 - 2 | Uppermill |
| 08/04/2000 | Golcar Utd | 0 - 2 | New Mill 94 |
| 11/04/2000 | Lindley | 2 - 1 | New Mill 94 |
| 15/04/2000 | New Mill 94 | 1 - 1 | Netherton |
| 22/04/2000 | H.V.Academicals | 0 - 7 | New Mill 94 |
| 29/04/2000 | Netherton | 0 - 2 | New Mill 94 |