| Division Three | |||
| 01/09/1999 | Little John | 3 - 3 | Cumberworth |
| 04/09/1999 | Cumberworth | 2 - 1 | Uppermill |
| 11/09/1999 | Cumberworth | 2 - 2 | New Mill 94 |
| 18/09/1999 | Black Star | 2 - 2 | Cumberworth |
| 25/09/1999 | Cumberworth | 0 - 1 | Netherton |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | New Mill 94 | 7 - 2 | Cumberworth |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Prospect (WL) | 3 - 6 | Cumberworth |
| 23/10/1999 | Golcar Utd | 2 - 5 | Cumberworth |
| 30/10/1999 | Cumberworth | 5 - 1 | Flockton FC |
| 06/11/1999 | Cumberworth | 2 - 0 | Golcar Utd |
| Groom Cup Round One | |||
| 13/11/1999 | Cumberworth | P - P | Walkers Arms |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Cumberworth | 3 - 0 | Black Star |
| 27/11/1999 | Cravens | 1 - 7 | Cumberworth |
| Groom Cup Round Two | |||
| 08/01/2000 | Cumberworth | 4 - 3 | Laund Hill YMCA |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Cumberworth | 0 - 5 | Little John |
| 22/01/2000 | New Mill 94 | 2 - 1 | Cumberworth |
| 05/02/2000 | Lindley | 4 - 3 | Cumberworth |
| 12/02/2000 | Cumberworth | 5 - 2 | Lindley |
| 19/02/2000 | Cumberworth | 4 - 1 | Black Star |
| 26/02/2000 | Netherton | 3 - 1 | Cumberworth |
| 04/03/2000 | Cumberworth | 2 - 2 | Cartworth Moor |
| 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 | Flockton FC | 1 - 1 | Cumberworth |
| 01/04/2000 | Cartworth Moor | 0 - 13 | Cumberworth |
| Groom Cup Semi Final | |||
| 04/04/2000 | Cumberworth | P - P | Netherton |
| 08/04/2000 | Cumberworth | 1 - 1 | H.V.Academicals |
| 11/04/2000 | Cumberworth | 2 - 1 | Little John |
| 15/04/2000 | Uppermill | 3 - 0 | Cumberworth |
| 18/04/2000 | KKS Ashbrow | 2 - 0 | Cumberworth |
| 22/04/2000 | Cumberworth | 0 - 2 | Cravens |
| Groom Cup Final | |||
| 25/04/2000 | Weavers | 1 - 1 | Cumberworth |
| 29/04/2000 | H.V.Academicals | 5 - 5 | Cumberworth |