| Division Three | |||
| 25/08/1999 | Flockton FC | 3 - 1 | KKS Ashbrow |
| 01/09/1999 | KKS Ashbrow | 0 - 1 | H.V.Academicals |
| 04/09/1999 | Cravens | 2 - 5 | KKS Ashbrow |
| 11/09/1999 | KKS Ashbrow | 4 - 3 | Cartworth Moor |
| FA Challenge Cup Round One | |||
| 18/09/1999 | Colne Valley BP | 1 - 12 | KKS Ashbrow |
| 25/09/1999 | Little John | 2 - 3 | KKS Ashbrow |
| 02/10/1999 | KKS Ashbrow | 2 - 2 | Uppermill |
| 09/10/1999 | Black Star | 1 - 1 | KKS Ashbrow |
| 16/10/1999 | KKS Ashbrow | 4 - 0 | Golcar Utd |
| 23/10/1999 | KKS Ashbrow | 0 - 0 | Black Star |
| 30/10/1999 | Netherton | 6 - 1 | KKS Ashbrow |
| 06/11/1999 | KKS Ashbrow | 4 - 3 | Lindley |
| Groom Cup Preliminary Round | |||
| 13/11/1999 | KKS Ashbrow | 3 - 2 | Upperthong SC |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | KKS Ashbrow | 0 - 4 | Lindley Liberal |
| 27/11/1999 | New Mill 94 | 3 - 1 | KKS Ashbrow |
| Groom Cup Round One | |||
| 08/01/2000 | KKS Ashbrow | 4 - 3 | Lindley |
| 15/01/2000 | Cartworth Moor | 2 - 3 | KKS Ashbrow |
| 22/01/2000 | Lindley | 2 - 3 | KKS Ashbrow |
| 29/01/2000 | H.V.Academicals | 2 - 1 | KKS Ashbrow |
| 05/02/2000 | KKS Ashbrow | 7 - 0 | Cravens |
| Groom Cup Round Two | |||
| 12/02/2000 | KKS Ashbrow | 4 - 2 | Golcar Utd |
| 19/02/2000 | Uppermill | 3 - 4 | KKS Ashbrow |
| 26/02/2000 | KKS Ashbrow | 5 - 3 | Little John |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2000 | Cumberworth | 3 - 2 | KKS Ashbrow |
| 18/03/2000 | Cumberworth | 2 - 1 | KKS Ashbrow |
| 25/03/2000 | KKS Ashbrow | 1 - 3 | New Mill 94 |
| 01/04/2000 | KKS Ashbrow | 4 - 1 | Flockton FC |
| 08/04/2000 | KKS Ashbrow | 2 - 0 | Netherton |
| 18/04/2000 | KKS Ashbrow | 2 - 0 | Cumberworth |
| 22/04/2000 | Golcar Utd | 6 - 5 | KKS Ashbrow |