| Division Two | |||
| 25/08/1999 | Lockwood | 1 - 2 | Hepworth Utd |
| 01/09/1999 | Hepworth Utd | 4 - 1 | Meltham Athletic |
| 04/09/1999 | Hepworth Utd | 1 - 4 | Sovereign Sports |
| 11/09/1999 | Scissett | 1 - 3 | Hepworth Utd |
| FA Challenge Cup Preliminary Round | |||
| 18/09/1999 | H.V.Academicals | 1 - 3 | Hepworth Utd |
| 25/09/1999 | Slaithwaite Utd | 1 - 0 | Hepworth Utd |
| 02/10/1999 | Hepworth Utd | 1 - 3 | Grange Moor |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Hepworth Utd | 1 - 2 | Darfield Cross Keys |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Hepworth Utd | 6 - 2 | Paddock Rangers |
| 23/10/1999 | Hepworth Utd | 2 - 1 | Lindley Liberal |
| 30/10/1999 | Hepworth Utd | 2 - 2 | Diggle |
| 06/11/1999 | Diggle | 3 - 3 | Hepworth Utd |
| Barlow Cup Round One | |||
| 13/11/1999 | Brackenhall Utd | 3 - 1 | Hepworth Utd |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Lepton Highlanders | 1 - 2 | Hepworth Utd |
| 27/11/1999 | Hepworth Utd | 2 - 2 | Mount |
| 08/01/2000 | Lepton Highlanders | 4 - 2 | Hepworth Utd |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Hepworth Utd | 2 - 2 | Holmbridge |
| 22/01/2000 | Hepworth Utd | 5 - 0 | Lockwood |
| 05/02/2000 | Lindley Liberal | 1 - 2 | Hepworth Utd |
| FA Challenge Cup Round Three | |||
| 19/02/2000 | Hepworth Utd | 5 - 1 | Holmbridge |
| 26/02/2000 | Hepworth Utd | 0 - 1 | Slaithwaite Utd |
| 04/03/2000 | Grange Moor | 3 - 0 | Hepworth Utd |
| 11/03/2000 | Mount | 2 - 4 | Hepworth Utd |
| FA Challenge Cup Round Four Quarter Final | |||
| 18/03/2000 | Hepworth Utd | 1 - 2 | Marsden (WR) |
| 25/03/2000 | Meltham Athletic | 2 - 1 | Hepworth Utd |
| 01/04/2000 | Hepworth Utd | 7 - 1 | Shelley |
| 08/04/2000 | Hepworth Utd | 7 - 2 | Lepton Highlanders |
| 11/04/2000 | Hepworth Utd | 0 - 2 | Berry Brow Lib |
| 15/04/2000 | Scholes | 1 - 1 | Hepworth Utd |
| 18/04/2000 | Berry Brow Lib | 0 - 1 | Hepworth Utd |
| 20/04/2000 | Shelley | 0 - 6 | Hepworth Utd |
| 22/04/2000 | Hepworth Utd | 1 - 3 | Scissett |
| 25/04/2000 | Hepworth Utd | 2 - 2 | Scholes |
| 29/04/2000 | Sovereign Sports | 3 - 1 | Hepworth Utd |