Leicestershire Challenge Cup 1990/91
Leicester City beat Hinckley Town in the final.
Quarter Finals > Semi Finals > Final
Entries – 8 Teams
Football League (1 team)
Leicester City .
Southern Football League (2 teams)
Hinckley Town and Leicester United.
Northern Premier League (1 team)
Shepshed Charterhouse.
Central Midlands League (1 team)
Highfield Rangers.
West Midlands (Regional) League (1 team)
Hinckley Athletic.
Leicestershire Senior League (2 teams)
Lutterworth Town and St. Andrews.
Quarter Finals
| 15th August 1990 | ||
| St. Andrews | 0 – 3 | Hinckley Town |
| 29th August 1990 | ||
| Highfield Rangers | 1 – 1 | Leicester United |
| 13th September 1990 | ||
| Shepshed Charterhouse | 1 – 1 | Hinckley Athletic |
| Date unknown. | ||
| Lutterworth Town | 1 – 5 | Leicester City |
Replays
| 6th September 1990 | ||
| Leicester United | 5 – 0 | Highfield Rangers |
| 20th December 1990 | ||
| Hinckley Athletic | 0 – 3 | Shepshed Charterhouse |
Semi Finals
| 14th March 1991 | ||
| Leicester United (Southern Football League – Midland) | 0 – 3 | Leicester City (Football League – Div 2) |
| 27th March 1991 | ||
| Hinckley Town (Southern Football League – Midland) | 2 – 0 | Shepshed Charterhouse (Northern Premier League – Prem) |
Final
| 2nd May 1991 | ||
| Leicester City (Football League – Div 2) | 2 – 1 | Hinckley Town (Southern Football League – Midland) at Filbert Street, Leicester. |