| Division Two | |||
| 03/09/2005 | Hepworth Utd | 3 - 2 | Mount |
| Sheffield Junior Challenge Cup Round One | |||
| 10/09/2005 | Hepworth Utd | 10 - 0 | Skelmanthorpe |
| 17/09/2005 | Hepworth Utd | 2 - 3 | Holmbridge |
| 24/09/2005 | Newsome WMC | 2 - 3 | Hepworth Utd |
| 01/10/2005 | Aimbry | 3 - 3 | Hepworth Utd |
| Sheffield Junior Challenge Cup Round Two | |||
| 08/10/2005 | Raggy Lads | 0 - 3 | Hepworth Utd |
| FA Challenge Cup Round One | |||
| 15/10/2005 | Hepworth Utd | 7 - 3 | Cravens |
| 22/10/2005 | Hepworth Utd | 4 - 2 | Kirkheaton Rovers |
| 29/10/2005 | Moldgreen | 4 - 2 | Hepworth Utd |
| 05/11/2005 | KKS Ashbrow | 2 - 1 | Hepworth Utd |
| Sheffield Junior Challenge Cup Round Three | |||
| 12/11/2005 | New Mill 94 | 1 - 2 | Hepworth Utd |
| FA Challenge Cup Round Two | |||
| 19/11/2005 | KKS Ashbrow | 0 - 1 | Hepworth Utd |
| 26/11/2005 | Hepworth Utd | 0 - 3 | Slaithwaite Utd |
| Sheffield Junior Challenge Cup Round Four | |||
| 10/12/2005 | Hepworth Utd | 2 - 3 | Telecon Sports FC |
| Barlow Cup Round One | |||
| 17/12/2005 | Hepworth Utd | 4 - 1 | Sovereign Sports |
| 07/01/2006 | Mount | 0 - 0 | Hepworth Utd |
| Barlow Cup Round Two | |||
| 14/01/2006 | Staithwaite Utd | 5 - 4 | Hepworth Utd |
| 28/01/2006 | Hepworth Utd | 0 - 3 | Newsome WMC |
| 04/02/2006 | Holmbridge | 0 - 1 | Hepworth Utd |
| 11/02/2006 | Hepworth Utd | 4 - 3 | Netherton |
| FA Challenge Cup Round Three | |||
| 18/02/2006 | Hepworth Utd | 2 - 3 | Collegians |
| 25/02/2006 | Hepworth Utd | 5 - 4 | Moldgreen |
| 11/03/2006 | Hepworth Utd | 4 - 4 | KKS Ashbrow |
| 18/03/2006 | Hepworth Utd | 2 - 2 | Aimbry |
| 25/03/2006 | Skelmanthorpe | 1 - 6 | Hepworth Utd |
| 08/04/2006 | Kirkheaton Rovers | 1 - 0 | Hepworth Utd |
| 11/04/2006 | Lindley Liberal | 1 - 2 | Hepworth Utd |
| 15/04/2006 | Hepworth Utd | 3 - 2 | Heyside FC |
| 18/04/2006 | Slaithwaite Utd | 2 - 4 | Hepworth Utd |
| 20/04/2006 | Hepworth Utd | 4 - 0 | Skelmanthorpe |
| 22/04/2006 | Heyside FC | 3 - 0 | Hepworth Utd |
| 25/04/2006 | Hepworth Utd | 2 - 4 | Lindley Liberal |
| 29/04/2006 | Netherton | 0 - 5 | Hepworth Utd |