| Division One | |||
| 25/08/1999 | Heywood Sports | 2 - 3 | Shepley |
| 01/09/1999 | Shepley | 3 - 3 | Almondbury Utd |
| 04/09/1999 | Skelmanthorpe | 1 - 1 | Shepley |
| 11/09/1999 | Wooldale Wanderers | 3 - 0 | Shepley |
| 18/09/1999 | Shepley | 2 - 0 | Kirkheaton Rovers |
| 25/09/1999 | Honley | 3 - 4 | Shepley |
| 02/10/1999 | Shepley | 2 - 2 | Kirkburton |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Silkstone Utd | 1 - 4 | Shepley |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Shepley | 3 - 1 | Britannia Sports |
| 23/10/1999 | Shepley | 3 - 1 | Storthes Hall |
| 30/10/1999 | Shepley | 2 - 4 | Brackenhall Utd |
| 06/11/1999 | Marsden | 1 - 4 | Shepley |
| Sheffield Junior Trophy Round Three | |||
| 13/11/1999 | The Archers FC | 2 - 0 | Shepley |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Shepley | 1 - 2 | Skelmanthorpe |
| 27/11/1999 | Shepley | 0 - 1 | Honley |
| 04/12/1999 | Kirkburton | 3 - 2 | Shepley |
| 08/01/2000 | Shepley | 3 - 1 | Marsden |
| 15/01/2000 | Kirkheaton Rovers | 2 - 1 | Shepley |
| Barlow Cup Round One | |||
| 22/01/2000 | Shepley | 4 - 0 | Storthes Hall |
| 05/02/2000 | Shepley | 1 - 1 | Skelmanthorpe |
| 19/02/2000 | Almondbury Utd | 3 - 0 | Shepley |
| 26/02/2000 | Brackenhall Utd | 6 - 3 | Shepley |
| 04/03/2000 | Storthes Hall | 2 - 1 | Shepley |
| Barlow Cup Round Two | |||
| 11/03/2000 | Skelmanthorpe | 1 - 2 | Shepley |
| 18/03/2000 | Shepley | 1 - 1 | Britannia Sports |
| Barlow Cup Round Three Quarter Final | |||
| 25/03/2000 | Shepley | 0 - 1 | Honley |
| 01/04/2000 | Shepley | 0 - 2 | Wooldale Wanderers |
| 15/04/2000 | Shepley | 0 - 3 | Heywood Sports |
| 22/04/2000 | Britannia Sports | 1 - 2 | Shepley |