| Division Four | |||
| 11/09/1999 | Holmbridge | 4 - 2 | Hade Edge |
| 18/09/1999 | Netherthong | 0 - 5 | Holmbridge |
| 25/09/1999 | Scapegoat Hill Utd | 2 - 0 | Holmbridge |
| 02/10/1999 | Holmbridge | 2 - 2 | Aimbry |
| Sheffield Junior Trophy Round Two | |||
| 09/10/1999 | Holmbridge | P - P | Squires FC |
| FA Challenge Cup Round One | |||
| 16/10/1999 | Lockwood | 2 - 4 | Holmbridge |
| 23/10/1999 | Holmbridge | 2 - 2 | The Stag FC |
| 30/10/1999 | Holmbridge | 2 - 1 | G.P.O. Sports |
| 06/11/1999 | Holmbridge | 2 - 3 | Weavers |
| Sheffield Junior Trophy Round Three | |||
| 13/11/1999 | Hillsborough FC | 3 - 1 | Holmbridge |
| FA Challenge Cup Round Two | |||
| 20/11/1999 | Thongsbridge Ath | 0 - 6 | Holmbridge |
| 27/11/1999 | Woodman | 0 - 4 | Holmbridge |
| Groom Cup Round One | |||
| 08/01/2000 | Woodman | 1 - 2 | Holmbridge |
| FA Challenge Cup Round Three | |||
| 15/01/2000 | Hepworth Utd | 2 - 2 | Holmbridge |
| 29/01/2000 | Hade Edge | 2 - 0 | Holmbridge |
| 05/02/2000 | Holmbridge | 4 - 3 | Netherthong |
| Groom Cup Round Two | |||
| 12/02/2000 | Holmbridge | 4 - 2 | Aimbry |
| FA Challenge Cup Round Three | |||
| 19/02/2000 | Hepworth Utd | 5 - 1 | Holmbridge |
| 26/02/2000 | Holmbridge | 2 - 2 | Upperthong SC |
| 04/03/2000 | The Stag FC | 1 - 1 | Holmbridge |
| Groom Cup Round Three Quarter Final | |||
| 11/03/2000 | Holmbridge | 1 - 4 | Netherton |
| 18/03/2000 | Walkers Arms | 1 - 2 | Holmbridge |
| 25/03/2000 | Holmbridge | 2 - 3 | Scapegoat Hill Utd |
| 01/04/2000 | Holmbridge | 10 - 4 | Walkers Arms |
| 08/04/2000 | G.P.O. Sports | 0 - 2 | Holmbridge |
| 15/04/2000 | Holmbridge | 5 - 0 | Woodman |
| 18/04/2000 | Aimbry | 3 - 1 | Holmbridge |
| 22/04/2000 | Weavers | 5 - 1 | Holmbridge |
| 27/04/2000 | Upperthong SC | 4 - 2 | Holmbridge |