| Division One | |||
| 25/08/1999 | Heywood Sports | 2 - 3 | Shepley |
| 01/09/1999 | Brackenhall Utd | 3 - 2 | Heywood Sports |
| 04/09/1999 | Heywood Sports | 0 - 1 | Kirkburton |
| 11/09/1999 | Heywood Sports | 1 - 0 | Storthes Hall |
| FA Challenge Cup Round One | |||
| 18/09/1999 | Lindley | 1 - 7 | Heywood Sports |
| 25/09/1999 | Heywood Sports | 2 - 0 | Skelmanthorpe |
| West Riding Challenge Cup Preliminary Round | |||
| 02/10/1999 | Heywood Sports | 5 - 1 | Lower Hopton |
| 09/10/1999 | Heywood Sports | 0 - 3 | Almondbury Utd |
| 16/10/1999 | Storthes Hall | 7 - 1 | Heywood Sports |
| 30/10/1999 | Heywood Sports | 4 - 4 | Marsden |
| West Riding Challenge Cup Round Two | |||
| 06/11/1999 | Heywood Sports | 1 - 0 | Crag Road Utd |
| Barlow Cup Round One | |||
| 13/11/1999 | Heywood Sports | 1 - 2 | Grange Moor |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Heywood Sports | 2 - 0 | Aimbry |
| 27/11/1999 | Britannia Sports | 3 - 1 | Heywood Sports |
| West Riding Challenge Cup Round Three | |||
| 11/12/1999 | Rawden / Crosshills | 0 - 3 | Heywood Sports |
| West Riding Challenge Cup Round Four | |||
| 08/01/2000 | Ardsley Celtic | 1 - 2 | Heywood Sports |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Zeneca (WR) | 3 - 4 | Heywood Sports |
| 22/01/2000 | Heywood Sports | 2 - 3 | Britannia Sports |
| 12/02/2000 | Marsden | 0 - 6 | Heywood Sports |
| 19/02/2000 | Heywood Sports | 3 - 2 | Kirkheaton Rovers |
| 26/02/2000 | Almondbury Utd | 1 - 0 | Heywood Sports |
| 04/03/2000 | Heywood Sports | 0 - 1 | Wooldale Wanderers |
| 11/03/2000 | Kirkburton | 2 - 1 | Heywood Sports |
| FA Challenge Cup Round Four Quarter Final | |||
| 18/03/2000 | Skelmanthorpe | 3 - 2 | Heywood Sports |
| 25/03/2000 | Wooldale Wanderers | 6 - 3 | Heywood Sports |
| 01/04/2000 | Kirkheaton Rovers | 2 - 1 | Heywood Sports |
| 08/04/2000 | Heywood Sports | 0 - 3 | Honley |
| 11/04/2000 | Heywood Sports | 0 - 2 | Brackenhall Utd |
| 15/04/2000 | Shepley | 0 - 3 | Heywood Sports |
| 22/04/2000 | Honley | 2 - 1 | Heywood Sports |
| 25/04/2000 | Skelmanthorpe | 0 - 0 | Heywood Sports |