Leicestershire Challenge Cup 1988/89
City beat United in the final.
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.
West Midlands (Regional) League (2 teams)
Hinckley Athletic and Hinckley Town.
Leicestershire Senior League (3 teams)
Holwell Sports, Stapenhill and Wigston Fields.
Quarter Finals
| 25th August 1988 | ||
| Stapenhill | 2 – 4 | Leicester City |
| 5th September 1988 | ||
| Wigston Fields | 0 – 1 | Shepshed Charterhouse |
| 24th September 1988 | ||
| Holwell Sports | 1 – 0 | Hinckley Town |
| 4th October 1988 | ||
| Hinckley Athletic | 1 – 2 | Leicester United |
Semi Finals
| 25th January 1989 | ||
| Leicester City (Football League – Div 2) | 5 – 1 | Holwell Sports (Leicestershire Senior League – Prem) |
| 22nd March 1989 | ||
| Shepshed Charterhouse (Northern Premier League – Prem) | 1 – 2 | Leicester United (Southern Football League – Prem) |
Final
| 26th April 1989 | ||
| Leicester City (Football League – Div 2) | 4 – 2 | Leicester United (Southern Football League – Prem) at Filbert Street, Leicester. |