Leicestershire Challenge Cup 1989/90
Hinckley Town win against Shepshed Charterhouse.
Quarter Finals > Semi Finals > Final
Entries – 8 Teams
Football League (1 team)
Leicester City.
Southern Football League (1 team)
Leicester United.
Northern Premier League (1 team)
Shepshed Charterhouse .
Central Midlands League (1 team)
Melton Town.
West Midlands (Regional) League (2 teams)
Hinckley Athletic and Hinckley Town .
Leicestershire Senior League (2 teams)
Birstall United and Wigston Town.
Quarter Finals
| 23rd August 1989 | ||
| Shepshed Charterhouse | 5 – 0 | Melton Town |
| 27th September 1989 | ||
| Wigston Town | 0 – 3 | Leicester United |
| 31st October 1989 | ||
| Hinckley Athletic | 0 – 0 | Hinckley Town |
| Date unknown. | ||
| Leicester City | 1 – 1 | Birstall United |
Replays
| 23rd December 1989 | ||
| Hinckley Town | 3 – 1 | Hinckley Athletic |
| 29th March 1990 | ||
| Birstall United | 1 – 1 (3 – 4 pens) | Leicester City |
Semi Finals
| 20th March 1990 | ||
| Leicester United (Southern Football League – Midland) | 1 – 2 | Shepshed Charterhouse (Northern Premier League – Prem) |
| 12th April 1990 | ||
| Leicester City (Football League – Div 2) | 2 – 2 | Hinckley Town (West Mids Regional League – Prem) |
Replay
| 19th April 1990 | ||
| Hinckley Town (West Mids Regional League – Prem) | 1 – 1 (3 – 0 pens) | Leicester City (Football League – Div 2) |
Final
| 24th April 1990 | ||
| Hinckley Town (West Mids Regional League – Prem) | 2 – 1 | Shepshed Charterhouse (Northern Premier League – Prem) at Filbert Street, Leicester. |