| Division Two | |||
| 25/08/1999 | Slaithwaite Utd | 5 - 1 | Scissett |
| 01/09/1999 | Scissett | 2 - 1 | Grange Moor |
| 04/09/1999 | Lepton Highlanders | 2 - 6 | Scissett |
| 11/09/1999 | Scissett | 1 - 3 | Hepworth Utd |
| 18/09/1999 | Lockwood | 1 - 1 | Scissett |
| 25/09/1999 | Berry Brow Lib | 3 - 5 | Scissett |
| 02/10/1999 | Scissett | 1 - 0 | Lindley Liberal |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Scissett | 3 - 1 | Cartworth Moor |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Scissett | 3 - 1 | Deanhousemuir |
| 23/10/1999 | Scissett | 13 - 1 | Lockwood |
| 30/10/1999 | Meltham Athletic | 1 - 5 | Scissett |
| 06/11/1999 | Scissett | 0 - 2 | Lepton Highlanders |
| Sheffield Junior Trophy Round Three | |||
| 13/11/1999 | A.B.M. Over 35s | 3 - 2 | Scissett |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Scissett | 3 - 4 | Wooldale Wanderers |
| 27/11/1999 | Lindley Liberal | 2 - 0 | Scissett |
| Barlow Cup Round One | |||
| 08/01/2000 | Lockwood | 0 - 2 | Scissett |
| 15/01/2000 | Scissett | 6 - 0 | Scholes |
| 22/01/2000 | Scissett | 2 - 2 | Slaithwaite Utd |
| 05/02/2000 | Scissett | 2 - 2 | Mount |
| Barlow Cup Round Two | |||
| 12/02/2000 | Scissett | 2 - 6 | Brackenhall Utd |
| 19/02/2000 | Scissett | 1 - 2 | Diggle |
| 26/02/2000 | Scissett | 2 - 2 | Berry Brow Lib |
| 04/03/2000 | Mount | 3 - 3 | Scissett |
| 11/03/2000 | Scissett | 7 - 2 | Shelley |
| 18/03/2000 | Scholes | 2 - 3 | Scissett |
| 25/03/2000 | Grange Moor | 1 - 1 | Scissett |
| 01/04/2000 | Sovereign Sports | 2 - 3 | Scissett |
| 08/04/2000 | Shelley | 2 - 4 | Scissett |
| 11/04/2000 | Scissett | 1 - 2 | Meltham Athletic |
| 18/04/2000 | Scissett | 5 - 4 | Sovereign Sports |
| 22/04/2000 | Hepworth Utd | 1 - 3 | Scissett |
| 27/04/2000 | Diggle | 1 - 0 | Scissett |