| Reserve Division One | |||
| 01/09/1999 | Shelley | 2 - 1 | Berry Brow Lib |
| 04/09/1999 | Slaithwaite Utd | 3 - 2 | Shelley |
| 11/09/1999 | Heywood Sports | 3 - 0 | Shelley |
| FA Junior Cup Round One | |||
| 18/09/1999 | Little John | 1 - 4 | Shelley |
| 25/09/1999 | Kirkheaton Rovers | 3 - 0 | Shelley |
| 02/10/1999 | Shelley | 4 - 3 | Shepley |
| 09/10/1999 | Brackenhall Utd | 3 - 0 | Shelley |
| 16/10/1999 | Shelley | 0 - 3 | Kirkburton |
| 23/10/1999 | Shelley | 1 - 1 | Uppermill Res |
| 30/10/1999 | Kirkburton | 10 - 2 | Shelley |
| 06/11/1999 | Britannia Sports | 3 - 2 | Shelley |
| 13/11/1999 | Shelley | 0 - 2 | Brackenhall Utd |
| FA Junior Cup Round Two | |||
| 20/11/1999 | Shelley | 6 - 0 | Lepton Highlanders |
| 27/11/1999 | Shelley | 2 - 3 | Lindley Liberal |
| 18/12/1999 | Shelley | 0 - 2 | Almondbury Utd |
| 08/01/2000 | Lindley Liberal | 4 - 2 | Shelley |
| 15/01/2000 | Shelley | 1 - 3 | Honley |
| Richardson Cup Round One | |||
| 22/01/2000 | Shelley | 2 - 2 | Uppermill Res |
| 05/02/2000 | Shelley | 1 - 1 | Diggle |
| Richardson Cup Round One | |||
| 12/02/2000 | Uppermill Res | P - P | Shelley |
| 19/02/2000 | Berry Brow Lib | 0 - 3 | Shelley |
| 26/02/2000 | Shelley | 1 - 3 | Kirkheaton Rovers |
| 18/03/2000 | Honley | 2 - 2 | Shelley |
| FA Junior Cup Round Three Quarter Finals | |||
| 25/03/2000 | Almondbury Utd | 3 - 1 | Shelley |
| 01/04/2000 | Shelley | 3 - 2 | Britannia Sports |
| 06/04/2000 | Diggle | 2 - 1 | Shelley |
| 11/04/2000 | Shelley | 0 - 0 | Slaithwaite Utd |
| 15/04/2000 | Shelley | 3 - 3 | Heywood Sports |
| 22/04/2000 | Uppermill Res | 3 - 2 | Shelley |
| 27/04/2000 | Shepley | 3 - 0 | Shelley |
| 06/05/2000 | Almondbury Utd | 6 - 0 | Shelley |