| Division One | |||
| 25/08/1999 | Honley | 3 - 1 | Wooldale Wanderers |
| 01/09/1999 | Wooldale Wanderers | 6 - 0 | Britannia Sports |
| 11/09/1999 | Wooldale Wanderers | 3 - 0 | Shepley |
| FA Challenge Cup Round One | |||
| 18/09/1999 | Wooldale Wanderers | 10 - 3 | Laund Hill YMCA |
| 25/09/1999 | Kirkburton | 2 - 2 | Wooldale Wanderers |
| 02/10/1999 | Wooldale Wanderers | 12 - 1 | Marsden |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Hoyland Nether | P - P | Wooldale Wanderers |
| 16/10/1999 | Marsden | 3 - 13 | Wooldale Wanderers |
| 23/10/1999 | Wooldale Wanderers | 3 - 1 | Skelmanthorpe |
| 30/10/1999 | Storthes Hall | 1 - 3 | Wooldale Wanderers |
| 06/11/1999 | Wooldale Wanderers | 3 - 1 | Almondbury Utd |
| Sheffield Junior Trophy Round Three | |||
| 13/11/1999 | Malin FC | 0 - 6 | Wooldale Wanderers |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Scissett | 3 - 4 | Wooldale Wanderers |
| 27/11/1999 | Wooldale Wanderers | 7 - 1 | Kirkburton |
| 04/12/1999 | Kirkheaton Rovers | 2 - 2 | Wooldale Wanderers |
| FA Challenge Cup Round Three | |||
| 18/12/1999 | Lindley Liberal | 0 - 4 | Wooldale Wanderers |
| Barlow Cup Round One | |||
| 08/01/2000 | Wooldale Wanderers | 3 - 0 | Slaithwaite Utd |
| 15/01/2000 | Britannia Sports | 1 - 2 | Wooldale Wanderers |
| 05/02/2000 | Wooldale Wanderers | 3 - 0 | Brackenhall Utd |
| Barlow Cup Round Two | |||
| 12/02/2000 | Wooldale Wanderers | 5 - 0 | Mount |
| FA Challenge Cup Round Four Quarter Final | |||
| 19/02/2000 | Wooldale Wanderers | 3 - 1 | Little John |
| 26/02/2000 | Wooldale Wanderers | 7 - 1 | Kirkheaton Rovers |
| 04/03/2000 | Heywood Sports | 0 - 1 | Wooldale Wanderers |
| Barlow Cup Round Three Quarter Final | |||
| 11/03/2000 | Wooldale Wanderers | 6 - 2 | Lepton Highlanders |
| 18/03/2000 | Almondbury Utd | 2 - 3 | Wooldale Wanderers |
| 25/03/2000 | Wooldale Wanderers | 6 - 3 | Heywood Sports |
| 01/04/2000 | Shepley | 0 - 2 | Wooldale Wanderers |
| 08/04/2000 | Skelmanthorpe | 1 - 4 | Wooldale Wanderers |
| FA Challenge Cup Semi Final | |||
| 14/04/2000 | Wooldale Wanderers | P - P | Marsden (WR) |
| 18/04/2000 | Wooldale Wanderers | 2 - 2 | Honley |
| 20/04/2000 | Wooldale Wanderers | 3 - 0 | Storthes Hall |
| Barlow Cup Semi Final | |||
| 24/04/2000 | Wooldale Wanderers | P - P | Brackenhall Utd |
| FA Challenge Cup Semi Final | |||
| 27/04/2000 | Wooldale Wanderers | 1 - 2 | Marsden (WR) |
| 06/05/2000 | Brackenhall Utd | 7 - 0 | Wooldale Wanderers |