Leicestershire Challenge Cup 1985/86
Shepshed Charterhouse hit six against Leicester United in the final.
Quarter Finals > Semi Finals > Final
Entries – 8 Teams
Southern Football League (2 teams)
Leicester United and Shepshed Charterhouse .
West Midlands (Regional) League (1 team)
Hinckley Athletic.
Leicestershire Senior League (5 teams)
Anstey Nomads, Friar Lane Old Boys, Holwell Works, Thringstone and Wigston Fields.
Quarter Finals
| 2nd April 1986 | ||
| Holwell Works | 1 – 4 | Shepshed Charterhouse |
| 3rd April 1986 | ||
| Friar Lane Old Boys | 1 – 4 | Hinckley Athletic |
| Thringstone | 0 – 3 | Leicester United |
| Wigston Fields | 0 – 1 | Anstey Nomads |
Semi Finals
| 15th April 1986 | ||
| Anstey Nomads (Leicestershire Senior League – Prem) | 2 – 4 | Leicester United (Southern Football League – Midland) |
| Shepshed Charterhouse (Southern Football League – Prem) | 1 – 0 | Hinckley Athletic (West Mids Regional League – Prem) |
Final
| 24th April 1986 | ||
| Shepshed Charterhouse (Southern Football League – Prem) | 6 – 0 | Leicester United (Southern Football League – Midland) at Filbert Street, Leicester. |