| Division Two | |||
| 25/08/1999 | Lepton Highlanders | 3 - 3 | Meltham Athletic |
| 01/09/1999 | Sovereign Sports | 5 - 1 | Lepton Highlanders |
| 04/09/1999 | Lepton Highlanders | 2 - 6 | Scissett |
| 11/09/1999 | Scholes | 1 - 5 | Lepton Highlanders |
| 18/09/1999 | Lepton Highlanders | 1 - 2 | Slaithwaite Utd |
| 25/09/1999 | Grange Moor | 1 - 0 | Lepton Highlanders |
| West Riding Challenge Trophy Round One | |||
| 02/10/1999 | Mount | 3 - 2 | Lepton Highlanders |
| 09/10/1999 | Lepton Highlanders | 1 - 3 | Diggle |
| FA Challenge Cup Round One | |||
| 16/10/1999 | G.P.O. Sports | 1 - 2 | Lepton Highlanders |
| 23/10/1999 | Diggle | 2 - 3 | Lepton Highlanders |
| 30/10/1999 | Lepton Highlanders | 1 - 0 | Berry Brow Lib |
| 06/11/1999 | Scissett | 0 - 2 | Lepton Highlanders |
| Barlow Cup Round Two | |||
| 13/11/1999 | Marsden | 0 - 5 | Lepton Highlanders |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Lepton Highlanders | 1 - 2 | Hepworth Utd |
| 27/11/1999 | Lepton Highlanders | 2 - 0 | Shelley |
| 18/12/1999 | Mount | 1 - 0 | Lepton Highlanders |
| 08/01/2000 | Lepton Highlanders | 4 - 2 | Hepworth Utd |
| 15/01/2000 | Lindley Liberal | 1 - 3 | Lepton Highlanders |
| 22/01/2000 | Meltham Athletic | 3 - 6 | Lepton Highlanders |
| 05/02/2000 | Berry Brow Lib | 2 - 4 | Lepton Highlanders |
| 12/02/2000 | Lepton Highlanders | 2 - 1 | Scholes |
| 19/02/2000 | Lepton Highlanders | 7 - 1 | Lockwood |
| 26/02/2000 | Lepton Highlanders | 2 - 2 | Grange Moor |
| 04/03/2000 | Lepton Highlanders | 2 - 3 | Lindley Liberal |
| Barlow Cup Round Three Quarter Final | |||
| 11/03/2000 | Wooldale Wanderers | 6 - 2 | Lepton Highlanders |
| 18/03/2000 | Slaithwaite Utd | 3 - 0 | Lepton Highlanders |
| 25/03/2000 | Shelley | 2 - 5 | Lepton Highlanders |
| 01/04/2000 | Lepton Highlanders | 5 - 2 | Mount |
| 08/04/2000 | Hepworth Utd | 7 - 2 | Lepton Highlanders |
| 15/04/2000 | Lockwood | 2 - 4 | Lepton Highlanders |
| 04/05/2000 | Lepton Highlanders | 0 - 5 | Sovereign Sports |