| Division Two | |||
| 25/08/1999 | Shelley | 1 - 3 | Diggle |
| 01/09/1999 | Diggle | 2 - 0 | Lockwood |
| 04/09/1999 | Meltham Athletic | 1 - 1 | Diggle |
| 11/09/1999 | Diggle | 2 - 3 | Sovereign Sports |
| FA Challenge Cup Preliminary Round | |||
| 18/09/1999 | Diggle | P - P | Woodman |
| 25/09/1999 | Scholes | 3 - 4 | Diggle |
| 02/10/1999 | Diggle | 3 - 3 | Slaithwaite Utd |
| 09/10/1999 | Lepton Highlanders | 1 - 3 | Diggle |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Diggle | 4 - 3 | Meltham Athletic |
| 23/10/1999 | Diggle | 2 - 3 | Lepton Highlanders |
| 30/10/1999 | Hepworth Utd | 2 - 2 | Diggle |
| 06/11/1999 | Diggle | 3 - 3 | Hepworth Utd |
| 13/11/1999 | Diggle | 5 - 0 | Shelley |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Kirkheaton Rovers | 1 - 5 | Diggle |
| 27/11/1999 | Diggle | 3 - 1 | Berry Brow Lib |
| Barlow Cup Round Two | |||
| 08/01/2000 | Honley | 2 - 1 | Diggle |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Diggle | 1 - 3 | Brackenhall Utd |
| 22/01/2000 | Diggle | 5 - 1 | Scholes |
| 05/02/2000 | Diggle | 6 - 3 | Meltham Athletic |
| 12/02/2000 | Lindley Liberal | 4 - 2 | Diggle |
| 19/02/2000 | Scissett | 1 - 2 | Diggle |
| 26/02/2000 | Diggle | 1 - 0 | Mount |
| 04/03/2000 | Slaithwaite Utd | 1 - 4 | Diggle |
| 11/03/2000 | Diggle | 1 - 3 | Grange Moor |
| 18/03/2000 | Grange Moor | 3 - 2 | Diggle |
| 25/03/2000 | Mount | 2 - 0 | Diggle |
| 01/04/2000 | Lockwood | 0 - 5 | Diggle |
| 08/04/2000 | Sovereign Sports | 0 - 1 | Diggle |
| 13/04/2000 | Diggle | 3 - 2 | Lindley Liberal |
| 22/04/2000 | Berry Brow Lib | 0 - 5 | Diggle |
| 27/04/2000 | Diggle | 1 - 0 | Scissett |