| Reserve Division Two | |||
| 25/08/1999 | New Mill 94 | 5 - 0 | Scholes |
| 01/09/1999 | New Mill 94 | 0 - 1 | Skelmanthorpe |
| 04/09/1999 | Wooldale Wanderers | 2 - 1 | New Mill 94 |
| 11/09/1999 | New Mill 94 | P - P | Diggle A |
| 18/09/1999 | Honley 'A' | 0 - 1 | New Mill 94 |
| 25/09/1999 | New Mill 94 | 1 - 2 | Marsden |
| 02/10/1999 | New Mill 94 | 3 - 0 | Kirkheaton Rovers 'A' |
| 09/10/1999 | Netherton | 3 - 6 | New Mill 94 |
| 16/10/1999 | Diggle A | 3 - 2 | New Mill 94 |
| 23/10/1999 | New Mill 94 | 2 - 3 | Sovereign Sports |
| 30/10/1999 | Scissett | 1 - 2 | New Mill 94 |
| 06/11/1999 | New Mill 94 | 5 - 0 | Almondbury Utd 'A' |
| Richardson Cup Round One | |||
| 13/11/1999 | Honley 'A' | 3 - 4 | New Mill 94 |
| 20/11/1999 | Uppermill 'A' | 1 - 2 | New Mill 94 |
| 27/11/1999 | Almondbury Utd 'A' | 3 - 6 | New Mill 94 |
| Richardson Cup Round Two | |||
| 08/01/2000 | New Mill 94 | 3 - 0 | Diggle |
| 15/01/2000 | Marsden | 1 - 5 | New Mill 94 |
| 22/01/2000 | Scholes | 1 - 5 | New Mill 94 |
| 05/02/2000 | New Mill 94 | 4 - 3 | Wooldale Wanderers |
| Richardson Cup Round Three Quarter Final | |||
| 12/02/2000 | New Mill 94 | 1 - 2 | Brackenhall Utd |
| 19/02/2000 | New Mill 94 | 5 - 0 | Honley 'A' |
| 26/02/2000 | Lockwood | 2 - 3 | New Mill 94 |
| 04/03/2000 | New Mill 94 | 7 - 3 | Uppermill 'A' |
| 18/03/2000 | New Mill 94 | 6 - 2 | Scissett |
| 25/03/2000 | New Mill 94 | 4 - 0 | Lockwood |
| 01/04/2000 | Kirkheaton Rovers 'A' | 0 - 7 | New Mill 94 |
| 08/04/2000 | New Mill 94 | 3 - 0 | Netherton |
| 15/04/2000 | Sovereign Sports | 2 - 2 | New Mill 94 |
| 18/04/2000 | Skelmanthorpe | 3 - 2 | New Mill 94 |