| Division Three | |||
| 25/08/1999 | Uppermill | 1 - 1 | Little John |
| 01/09/1999 | Little John | 3 - 3 | Cumberworth |
| 04/09/1999 | Black Star | 2 - 3 | Little John |
| 11/09/1999 | Little John | 1 - 3 | Netherton |
| 18/09/1999 | New Mill 94 | 4 - 2 | Little John |
| 25/09/1999 | Little John | 2 - 3 | KKS Ashbrow |
| 02/10/1999 | Little John | 0 - 4 | Golcar Utd |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Little John | 5 - 1 | Shelley |
| 23/10/1999 | Little John | 2 - 4 | H.V.Academicals |
| 30/10/1999 | Cravens | 2 - 5 | Little John |
| 06/11/1999 | Little John | 3 - 3 | Cartworth Moor |
| 13/11/1999 | Little John | P - P | Lindley |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Little John | 3 - 2 | Sovereign Sports |
| 04/12/1999 | Little John | 0 - 1 | New Mill 94 |
| Groom Cup Round Two | |||
| 08/01/2000 | Little John | 1 - 2 | Weavers |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Cumberworth | 0 - 5 | Little John |
| 22/01/2000 | Little John | 2 - 1 | Cravens |
| 05/02/2000 | Little John | 3 - 0 | Black Star |
| 12/02/2000 | Netherton | 4 - 2 | Little John |
| FA Challenge Cup Round Four Quarter Final | |||
| 19/02/2000 | Wooldale Wanderers | 3 - 1 | Little John |
| 26/02/2000 | KKS Ashbrow | 5 - 3 | Little John |
| 04/03/2000 | Golcar Utd | 2 - 1 | Little John |
| 11/03/2000 | Lindley | 1 - 3 | Little John |
| 18/03/2000 | H.V.Academicals | 2 - 2 | Little John |
| 25/03/2000 | Cartworth Moor | 5 - 0 | Little John |
| 08/04/2000 | Little John | 2 - 5 | Uppermill |
| 11/04/2000 | Cumberworth | 2 - 1 | Little John |
| 18/04/2000 | Flockton FC | 4 - 3 | Little John |
| 29/04/2000 | Little John | 3 - 3 | Flockton FC |