| Division Three | |||
| 25/08/1999 | Black Star | 3 - 4 | Cartworth Moor |
| 01/09/1999 | Cartworth Moor | 2 - 4 | Netherton |
| 04/09/1999 | Cartworth Moor | 2 - 0 | Lindley |
| 11/09/1999 | KKS Ashbrow | 4 - 3 | Cartworth Moor |
| 18/09/1999 | Cartworth Moor | 1 - 1 | Golcar Utd |
| 25/09/1999 | Flockton FC | 6 - 2 | Cartworth Moor |
| 02/10/1999 | Cartworth Moor | 3 - 1 | H.V.Academicals |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Scissett | 3 - 1 | Cartworth Moor |
| 16/10/1999 | H.V.Academicals | 2 - 2 | Cartworth Moor |
| 23/10/1999 | Cartworth Moor | 0 - 4 | New Mill 94 |
| 30/10/1999 | Lindley | 1 - 1 | Cartworth Moor |
| 06/11/1999 | Little John | 3 - 3 | Cartworth Moor |
| Groom Cup Round One | |||
| 13/11/1999 | Cartworth Moor | 6 - 1 | Scapegoat Hill Utd |
| 20/11/1999 | Cravens | 4 - 2 | Cartworth Moor |
| 27/11/1999 | Cartworth Moor | 0 - 0 | Uppermill |
| 08/01/2000 | Cartworth Moor | 4 - 1 | Cravens |
| 15/01/2000 | Cartworth Moor | 2 - 3 | KKS Ashbrow |
| 22/01/2000 | Cartworth Moor | 6 - 1 | Black Star |
| 29/01/2000 | Netherton | 2 - 0 | Cartworth Moor |
| 05/02/2000 | Uppermill | 8 - 0 | Cartworth Moor |
| Groom Cup Round Two | |||
| 12/02/2000 | The Stag FC | 2 - 0 | Cartworth Moor |
| 19/02/2000 | Golcar Utd | 1 - 4 | Cartworth Moor |
| 26/02/2000 | Cartworth Moor | 0 - 0 | Flockton FC |
| 04/03/2000 | Cumberworth | 2 - 2 | Cartworth Moor |
| 18/03/2000 | New Mill 94 | 4 - 0 | Cartworth Moor |
| 25/03/2000 | Cartworth Moor | 5 - 0 | Little John |
| 01/04/2000 | Cartworth Moor | 0 - 13 | Cumberworth |