Leicestershire Challenge Cup 1965/66
Loughborough United beat Hinckley Athletic.
Entries – 4 Teams
Southern Football League (1 team)
Hinckley Athletic .
Midland Counties League (1 team)
Loughborough United .
Leicestershire Senior League (2 teams)
Enderby Town and Loughborough College.
Semi Finals
| 28th August 1965 | ||
| Loughborough United (Midland Counties League) | 2 – 0 | Enderby Town (Leicestershire Senior League – Div 1) |
| 16th October 1965 | ||
| Hinckley Athletic (Southern Football League – Div 1) | 4 – 1 | Loughborough College (Leicestershire Senior League – Div 1) |
Final
Played over two legs.
| 5th May 1966 | ||
| Hinckley Athletic (Southern Football League – Div 1) | 1 – 0 | Loughborough United (Midland Counties League) at Middlefield Lane, Hinckley. |
| 12th May 1966 | ||
| Loughborough United (Midland Counties League) | 2 – 0 | Hinckley Athletic (Southern Football League – Div 1) at Brown’s Lane, Loughborough. |