| Division Two | |||
| 30/08/2000 | Lindley Liberal | 2 - 1 | Lepton Highlanders |
| 06/09/2000 | Lepton Highlanders | 0 - 3 | Diggle |
| 09/09/2000 | New Mill 94 | 3 - 1 | Lepton Highlanders |
| 23/09/2000 | Uppermill | 3 - 3 | Lepton Highlanders |
| 30/09/2000 | Lepton Highlanders | 2 - 5 | Heywood Sports |
| West Riding Challenge Cup Round One | |||
| 14/10/2000 | Lepton Highlanders | 2 - 1 | Robin Hood Athletic |
| FA Challenge Cup Round One | |||
| 21/10/2000 | Lockwood | 1 - 3 | Lepton Highlanders |
| 28/10/2000 | Scissett | 6 - 1 | Lepton Highlanders |
| West Riding Challenge Cup Round Two | |||
| 04/11/2000 | Lepton Highlanders | 2 - 8 | Springhead |
| 25/11/2000 | Scholes | 2 - 5 | Lepton Highlanders |
| 02/12/2000 | Lepton Highlanders | 4 - 4 | Scholes |
| 23/12/2000 | Netherton | 5 - 1 | Lepton Highlanders |
| 06/01/2001 | Diggle | 4 - 2 | Lepton Highlanders |
| Barlow Cup Round Two | |||
| 13/01/2001 | Lepton Highlanders | 3 - 4 | New Mill 94 |
| 27/01/2001 | Lepton Highlanders | 2 - 2 | New Mill 94 |
| FA Challenge Cup Round Two | |||
| 03/02/2001 | Diggle | 6 - 2 | Lepton Highlanders |
| 17/02/2001 | Lepton Highlanders | 1 - 2 | Storthes Hall |
| 24/02/2001 | Lepton Highlanders | 7 - 1 | Berry Brow Lib |
| 17/03/2001 | Berry Brow Lib | 2 - 2 | Lepton Highlanders |
| 31/03/2001 | Heywood Sports | 1 - 1 | Lepton Highlanders |
| 05/04/2001 | Lepton Highlanders | 1 - 1 | Netherton |
| 10/04/2001 | Storthes Hall | 7 - 2 | Lepton Highlanders |
| 12/04/2001 | Lepton Highlanders | 3 - 1 | Marsden |
| 14/04/2001 | Lepton Highlanders | 1 - 1 | Lindley Liberal |
| 19/04/2001 | Lepton Highlanders | 2 - 3 | Mount |
| 21/04/2001 | Mount | 3 - 3 | Lepton Highlanders |
| 24/04/2001 | Lepton Highlanders | 3 - 1 | Scissett |
| 28/04/2001 | Hepworth Utd | 3 - 3 | Lepton Highlanders |
| 01/05/2001 | Lepton Highlanders | 0 - 0 | Hepworth Utd |
| 01/05/2001 | Marsden | 0 - 0 | Lepton Highlanders |
| 01/05/2001 | Lepton Highlanders | 0 - 0 | Uppermill |