| Division Two | |||
| 30/08/2000 | Storthes Hall | 2 - 1 | Diggle |
| 06/09/2000 | Lepton Highlanders | 0 - 3 | Diggle |
| 09/09/2000 | Diggle | 3 - 2 | Lindley Liberal |
| 23/09/2000 | New Mill 94 | 3 - 3 | Diggle |
| 30/09/2000 | Diggle | 2 - 0 | Mount |
| FA Challenge Cup Round One | |||
| 21/10/2000 | Diggle | 1 - 0 | Moldgreen |
| West Riding Challenge Cup Round One | |||
| 25/11/2000 | Diggle | 3 - 0 | Willowfield Celtic |
| West Riding Challenge Cup Round Two | |||
| 02/12/2000 | Diggle | 4 - 2 | Kirkby Malzeard |
| West Riding Challenge Cup Round Three | |||
| 23/12/2000 | Horsforth St Margarets | 5 - 0 | Diggle |
| 06/01/2001 | Diggle | 4 - 2 | Lepton Highlanders |
| Barlow Cup Round One | |||
| 13/01/2001 | Scholes | 0 - 1 | Diggle |
| 27/01/2001 | Hepworth Utd | 2 - 3 | Diggle |
| FA Challenge Cup Round Two | |||
| 03/02/2001 | Diggle | 6 - 2 | Lepton Highlanders |
| Barlow Cup Round Two | |||
| 10/02/2001 | Sovereign Sports | 0 - 1 | Diggle |
| 17/02/2001 | Mount | 1 - 3 | Diggle |
| 24/02/2001 | Diggle | 3 - 1 | Uppermill |
| FA Challenge Cup Round Three | |||
| 17/03/2001 | Honley | 2 - 1 | Diggle |
| 24/03/2001 | Diggle | 2 - 1 | Netherton |
| Barlow Cup Round Three Quarter Final | |||
| 31/03/2001 | Wooldale Wanderers | 3 - 2 | Diggle |
| 03/04/2001 | Berry Brow Lib | 1 - 1 | Diggle |
| 10/04/2001 | Diggle | 2 - 1 | Heywood Sports |
| 12/04/2001 | Netherton | 2 - 0 | Diggle |
| 14/04/2001 | Diggle | 3 - 1 | Storthes Hall |
| 17/04/2001 | Lindley Liberal | 2 - 2 | Diggle |
| 19/04/2001 | Diggle | 0 - 4 | Scissett |
| 24/04/2001 | Diggle | P - P | Berry Brow Lib |
| 26/04/2001 | Uppermill | 1 - 4 | Diggle |
| 28/04/2001 | Diggle | 2 - 1 | Scholes |
| 01/05/2001 | Scissett | 0 - 0 | Diggle |
| 01/05/2001 | Diggle | 0 - 0 | Hepworth Utd |
| 01/05/2001 | Marsden | 0 - 0 | Diggle |
| 01/05/2001 | Diggle | 0 - 0 | New Mill 94 |
| 01/05/2001 | Heywood Sports | 0 - 0 | Diggle |
| 01/05/2001 | Scholes | 0 - 0 | Diggle |
| 01/05/2001 | Diggle | 0 - 0 | Marsden |