Leicestershire Challenge Cup 1968/69
Oadby Town win the cup for the first time.
First Round > Semi Finals > Final
Entries – 6 Teams
Midland Counties League (1 team)
Loughborough United.
East Midlands (Regional) League (1 team)
Anstey Nomads.
West Midlands (Regional) League (1 team)
Hinckley Athletic.
Leicestershire Senior League (3 teams)
Enderby Town , Oadby Town and Wigston Fields.
First Round
| 1st April 1969 | ||
| Anstey Nomads | 1 – 1 | Oadby Town |
| 2nd April 1969 | ||
| Enderby Town | 2 – 1 | Loughborough United |
Replays
| 16th April 1969 | ||
| Oadby Town | 1 – 1 | Anstey Nomads |
| 23rd April 1969 | ||
| Anstey Nomads | 0 – 3 | Oadby Town |
Byes: Hinckley Athletic and Wigston Fields.
Semi Finals
| 1st May 1969 | ||
| Hinckley Athletic (West Mids Regional League – Prem) | 1 – 3 | Enderby Town (Leicestershire Senior League – Div 1) |
| 12th May 1969 | ||
| Oadby Town (Leicestershire Senior League – Div 1) | 5 – 1 | Wigston Fields (Leicestershire Senior League – Div 1) |
Final
Played over two legs.
| 14th May 1969 | ||
| Enderby Town (Leicestershire Senior League – Div 1) | 0 – 2 | Oadby Town (Leicestershire Senior League – Div 1) at George Street, Enderby. |
| 20th May 1969 | ||
| Oadby Town (Leicestershire Senior League – Div 1) | 0 – 1 | Enderby Town (Leicestershire Senior League – Div 1) at Wigston Road, Oadby. |