Westerby Challenge Cup 1999/00
Leicester City win against Barwell.
First Round > Quarter Finals > Semi Finals > Final
Entries – 12 Teams
FA Premier League (1 team)
Leicester City .
Southern Football League (2 teams)
Hinckley United and Shepshed Dynamo.
Midland Football Alliance (2 teams)
Barwell and Oadby Town.
Leicestershire Senior League (7 teams)
Birstall United, Highfield Rangers, Holwell Sports, Ibstock Welfare, Kirby Muxloe, Quorn and St. Andrews.
First Round
| 21st September 1999 | ||
| Holwell Sports | 5 – 0 | St. Andrews |
| 5th October 1999 | ||
| Shepshed Dynamo | 0 – 1 | Kirby Muxloe |
| 12th October 1999 | ||
| Barwell | 3 – 1 | Highfield Rangers |
| 19th October 1999 | ||
| Hinckley United | 3 – 1 | Quorn |
Byes: Birstall United, Ibstock Welfare, Leicester City and Oadby Town.
Quarter Finals
| 1st December 1999 | ||
| Barwell | 3 – 2 | Birstall United |
| 14th December 1999 | ||
| Holwell Sports | 1 – 3 | Oadby Town |
| 30th December 1999 | ||
| Kirby Muxloe | 0 – 2 | Hinckley United |
| Date unknown. | ||
| Leicester City | 2 – 0 | Ibstock Welfare |
Semi Finals
| Date unknown. | ||
| Barwell (Midland Football Alliance) | 1 – 0 | Oadby Town (Midland Football Alliance) at Holmes Park, Whetstone. |
| Hinckley United (Southern Football League – Western) | 0 – 2 | Leicester City (FA Premier League) at Holmes Park, Whetstone. |
Final
| 9th May 2000 | ||
| Leicester City (FA Premier League) | 4 – 0 | Barwell (Midland Football Alliance) at Filbert Street, Leicester. |