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