| Division Three | |||
| 25/08/1999 | Cravens | 0 - 5 | Netherton |
| 01/09/1999 | Lindley | 0 - 1 | Cravens |
| 04/09/1999 | Cravens | 2 - 5 | KKS Ashbrow |
| 11/09/1999 | Golcar Utd | 5 - 3 | Cravens |
| 18/09/1999 | Cravens | 2 - 6 | Flockton FC |
| 25/09/1999 | H.V.Academicals | 4 - 2 | Cravens |
| West Riding Challenge Trophy Round One | |||
| 02/10/1999 | Upper Armley OB | 3 - 2 | Cravens |
| 09/10/1999 | Cravens | 4 - 0 | Lindley |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Cravens | 3 - 4 | Lindley Liberal |
| 30/10/1999 | Cravens | 2 - 5 | Little John |
| 06/11/1999 | Uppermill | 3 - 2 | Cravens |
| Groom Cup Round One | |||
| 13/11/1999 | Netherthong | 1 - 4 | Cravens |
| 20/11/1999 | Cravens | 4 - 2 | Cartworth Moor |
| 27/11/1999 | Cravens | 1 - 7 | Cumberworth |
| 04/12/1999 | Black Star | 0 - 7 | Cravens |
| 08/01/2000 | Cartworth Moor | 4 - 1 | Cravens |
| Groom Cup Round Two | |||
| 15/01/2000 | Netherton | 6 - 3 | Cravens |
| 22/01/2000 | Little John | 2 - 1 | Cravens |
| 29/01/2000 | Cravens | 1 - 0 | Black Star |
| 05/02/2000 | KKS Ashbrow | 7 - 0 | Cravens |
| 12/02/2000 | Cravens | 0 - 5 | Uppermill |
| 19/02/2000 | Flockton FC | 6 - 1 | Cravens |
| 26/02/2000 | Cravens | 2 - 4 | H.V.Academicals |
| 04/03/2000 | Cravens | 2 - 2 | New Mill 94 |
| 11/03/2000 | New Mill 94 | 2 - 0 | Cravens |
| 18/03/2000 | Netherton | 0 - 0 | Cravens |
| 25/03/2000 | Cravens | 2 - 2 | Golcar Utd |
| 22/04/2000 | Cumberworth | 0 - 2 | Cravens |