| Saturday 11th November, 1989 |
| Sheffield & Hallamshire Senior Cup First Round |
| | Ash House |  | 2-1 |  | Yorkshire Main | |
| | Goldthorpe Colliery | | 1-0 |  | Hallam | |
| | Maltby Main |  | 3-2 |  | Parkgate | |
| | Mexborough Town |  | 0-4 | | Treble | |
| | Rossington Hasland | | 2-1 |  | Stocksbridge Park Steels | |
| | Sheffield |  | 6-2 |  | Kiveton Park | |
| | Sheffield Centralians | | 1-1 |  | Grimethorpe Miners Welfare | |
| | Woodhouse Stag | | 0-3 |  | Frecheville CA | |
| | Woolley Miners Welfare |  | 0-1 |  | Denaby United | |
| | Worsbrough Bridge Athletic |  | 4-1 |  | Brodsworth Welfare | |
|||||||
| Saturday 18th November, 1989 |
| Sheffield & Hallamshire Senior Cup First Round |
| | Dronfield United |  | 2-0 | | Caribbean Sports | |
| Sheffield & Hallamshire Senior Cup First Round Replay |
| | Sheffield Centralians | | L-L | | Grimethorpe Miners Welfare | |
| (Result not known - Sheffield Centralians progressed) |
|||||||
| Tuesday 5th December, 1989 |
| Sheffield & Hallamshire Senior Cup Second Round |
| | Denaby United | | 4-1 | | Frecheville CA | |
|||||||
| Saturday 9th December, 1989 |
| Sheffield & Hallamshire Senior Cup Second Round |
| | Harworth Colliery Institute |  | 5-1 | | Dronfield United | |
| | Maltby Main | | 3-1 | | Sheffield Centralians | |
| | Sheffield | | 2-2 | | Frickley Athletic | |
| | Worsbrough Bridge Athletic | | 4-2 | | Goldthorpe Colliery | |
|||||||
| Tuesday 12th December, 1989 |
| Sheffield & Hallamshire Senior Cup Second Round Replay |
| | Frickley Athletic | | 3-1 | | Sheffield | |
|||||||
| Saturday 13th January, 1990 |
| Sheffield & Hallamshire Senior Cup Third Round |
| | Denaby United | | 2-1 | | Ash House | |
| | Worsbrough Bridge Athletic | | 4-6 | | Maltby Main | |
|||||||
| Tuesday 6th February, 1990 |
| Sheffield & Hallamshire Senior Cup Semi-Finals First Leg |
| | Maltby Main | | 0-0 | | Frickley Athletic | |
|||||||
| Saturday 10th February, 1990 |
| Sheffield & Hallamshire Senior Cup Semi-Finals First Leg |
| | Denaby United | | 3-0 | | Harworth Colliery Institute | |
|||||||
| Tuesday 13th February, 1990 |
| Sheffield & Hallamshire Senior Cup Semi-Finals Second Leg |
| | Frickley Athletic | | 2-0 | | Maltby Main | |
| (Frickley Athletic won 2-0 on aggregate) |
|||||||
| Saturday 17th February, 1990 |
| Sheffield & Hallamshire Senior Cup Semi-Finals Second Leg |
| | Harworth Colliery Institute | | 1-3 | | Denaby United | |
| (Denaby United won 6-1 on aggregate) |
|||||||
| Monday 19th March, 1990 |
| Sheffield & Hallamshire Senior Cup Final First Leg |
| | Denaby United | | 1-0 | | Frickley Athletic | |
|||||||
| Monday 9th April, 1990 |
| Sheffield & Hallamshire Senior Cup Final Second Leg |
| | Frickley Athletic | | 2-0 | | Denaby United | |
| (Frickley Athletic won 2-1 on aggregate) |
FA Cup