Westerby Challenge Cup 1998/99
Leicester City score 10 against Oadby Town.
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 (1 team)
Barwell.
Leicestershire Senior League (8 teams)
Birstall United, Downes Sports, Friar Lane Old Boys, Holwell Sports, Ibstock Welfare, Kirby Muxloe, Oadby Town and St. Andrews.
First Round
| 13th October 1998 | ||
| Downes Sports | 1 – 3 | Barwell |
| Kirby Muxloe | 2 – 1 | Hinckley United |
| Date unknown. | ||
| Friar Lane Old Boys | 1 – 1 | Oadby Town |
| Holwell Sports | 1 – 2 | St. Andrews * |
Replays
| Date unknown. | ||
| Oadby Town | 4 – 0 | Friar Lane Old Boys |
Byes: Birstall United, Ibstock Welfare, Leicester City and Shepshed Dynamo.
Quarter Finals
| 28th October 1998 | ||
| Shepshed Dynamo | 1 – 3 | Leicester City |
| 25th November 1998 | ||
| Oadby Town | 2 – 0 | Barwell |
| Date unknown. | ||
| Birstall United | (walkover – home win) | St. Andrews |
| Kirby Muxloe | 1 – 2 | Ibstock Welfare |
Semi Finals
| 2nd March 1999 | ||
| Birstall United (Leicestershire Senior League – Prem) | 0 – 6 | Leicester City (FA Premier League) at Holmes Park, Whetstone. |
| Date unknown. | ||
| Oadby Town (Leicestershire Senior League – Prem) | 3 – 1 | Ibstock Welfare (Leicestershire Senior League – Prem) venue unknown. |
Final
| 19th April 1999 | ||
| Leicester City (FA Premier League) | 10 – 1 | Oadby Town (Leicestershire Senior League – Prem) at Filbert Street, Leicester. |