| Reserve Division Two | |||
| 25/08/1999 | Wooldale Wanderers | 3 - 2 | Almondbury Utd 'A' |
| 01/09/1999 | Lockwood | 1 - 0 | Wooldale Wanderers |
| 04/09/1999 | Wooldale Wanderers | 2 - 1 | New Mill 94 |
| 11/09/1999 | Skelmanthorpe | 1 - 0 | Wooldale Wanderers |
| 18/09/1999 | Scholes | 0 - 7 | Wooldale Wanderers |
| 25/09/1999 | Wooldale Wanderers | 2 - 1 | Diggle A |
| 02/10/1999 | Honley 'A' | 3 - 2 | Wooldale Wanderers |
| 09/10/1999 | Wooldale Wanderers | 9 - 2 | Marsden |
| FA Junior Cup Round One | |||
| 16/10/1999 | Wooldale Wanderers | 4 - 1 | Scissett |
| 23/10/1999 | Uppermill 'A' | 2 - 4 | Wooldale Wanderers |
| 30/10/1999 | Wooldale Wanderers | 5 - 2 | Netherton |
| 06/11/1999 | Sovereign Sports | 3 - 7 | Wooldale Wanderers |
| Richardson Cup Round One | |||
| 13/11/1999 | Lindley Liberal | 2 - 3 | Wooldale Wanderers |
| FA Junior Cup Round Two | |||
| 20/11/1999 | Heywood Sports | 3 - 4 | Wooldale Wanderers |
| 27/11/1999 | Scissett | 1 - 17 | Wooldale Wanderers |
| FA Junior Cup Round Three Quarter Finals | |||
| 18/12/1999 | Wooldale Wanderers | 12 - 0 | Hade Edge |
| 08/01/2000 | Netherton | 0 - 4 | Wooldale Wanderers |
| 15/01/2000 | Wooldale Wanderers | 9 - 0 | Scissett |
| Richardson Cup Round Two | |||
| 22/01/2000 | Wooldale Wanderers | 4 - 2 | Kirkheaton Rovers |
| 05/02/2000 | New Mill 94 | 4 - 3 | Wooldale Wanderers |
| 12/02/2000 | Wooldale Wanderers | 2 - 4 | Skelmanthorpe |
| 26/02/2000 | Almondbury Utd 'A' | 6 - 4 | Wooldale Wanderers |
| 04/03/2000 | Wooldale Wanderers | 7 - 0 | Scholes |
| Richardson Cup Round Three Quarter Final | |||
| 11/03/2000 | Kirkburton | 4 - 1 | Wooldale Wanderers |
| 25/03/2000 | Marsden | 0 - 2 | Wooldale Wanderers |
| FA Junior Cup Semi Final | |||
| 31/03/2000 | Kirkburton | 3 - 1 | Wooldale Wanderers |
| 06/04/2000 | Kirkheaton Rovers 'A' | 2 - 1 | Wooldale Wanderers |
| 11/04/2000 | Wooldale Wanderers | 4 - 1 | Sovereign Sports |
| 22/04/2000 | Wooldale Wanderers | 3 - 1 | Lockwood |
| 25/04/2000 | Wooldale Wanderers | 2 - 2 | Honley 'A' |
| 29/04/2000 | Wooldale Wanderers | 6 - 1 | Kirkheaton Rovers 'A' |
| 02/05/2000 | Diggle A | 5 - 3 | Wooldale Wanderers |
| / / | Wooldale Wanderers | P - P | Uppermill 'A' |