| Division Two | |||
| 25/08/1999 | Grange Moor | 5 - 1 | Sovereign Sports |
| 01/09/1999 | Scissett | 2 - 1 | Grange Moor |
| 04/09/1999 | Grange Moor | 2 - 3 | Scholes |
| 11/09/1999 | Slaithwaite Utd | 2 - 4 | Grange Moor |
| 18/09/1999 | Lindley Liberal | 2 - 2 | Grange Moor |
| 25/09/1999 | Grange Moor | 1 - 0 | Lepton Highlanders |
| 02/10/1999 | Hepworth Utd | 1 - 3 | Grange Moor |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Grange Moor | 0 - 3 | Hatfield Blue Bell |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Sovereign Sports | 3 - 1 | Grange Moor |
| 23/10/1999 | Berry Brow Lib | 1 - 4 | Grange Moor |
| 30/10/1999 | Grange Moor | 0 - 0 | Mount |
| 06/11/1999 | Shelley | 0 - 10 | Grange Moor |
| Barlow Cup Round One | |||
| 13/11/1999 | Heywood Sports | 1 - 2 | Grange Moor |
| 20/11/1999 | Grange Moor | 2 - 3 | Slaithwaite Utd |
| 27/11/1999 | Lockwood | 1 - 4 | Grange Moor |
| Barlow Cup Round Two | |||
| 08/01/2000 | Kirkburton | 2 - 1 | Grange Moor |
| 15/01/2000 | Grange Moor | 8 - 1 | Shelley |
| 22/01/2000 | Sovereign Sports | 1 - 0 | Grange Moor |
| 05/02/2000 | Scholes | 1 - 3 | Grange Moor |
| 19/02/2000 | Grange Moor | 3 - 1 | Lindley Liberal |
| 26/02/2000 | Lepton Highlanders | 2 - 2 | Grange Moor |
| 04/03/2000 | Grange Moor | 3 - 0 | Hepworth Utd |
| 11/03/2000 | Diggle | 1 - 3 | Grange Moor |
| 18/03/2000 | Grange Moor | 3 - 2 | Diggle |
| 25/03/2000 | Grange Moor | 1 - 1 | Scissett |
| 01/04/2000 | Grange Moor | 4 - 2 | Berry Brow Lib |
| 08/04/2000 | Grange Moor | 2 - 1 | Meltham Athletic |
| 15/04/2000 | Mount | 1 - 3 | Grange Moor |
| 29/04/2000 | Meltham Athletic | 1 - 2 | Grange Moor |
| 02/05/2000 | Grange Moor | 5 - 2 | Lockwood |