Westerby Challenge Cup 2018/19
Coalville Town beat Loughborough University in the final.
First Round > Quarter Finals > Semi Finals > Final
Entries – 16 Teams
Southern League (2 teams)
Barwell and Coalville Town .
Northern Premier League (1 team)
Loughborough Dynamo.
United Counties League (7 teams)
Anstey Nomads, Harborough Town, Kirby Muxloe, Leicester Nirvana, Lutterworth Town, Oadby Town and St. Andrews.
Midland Football League (6 teams)
Hinckley AFC, Leicester Road, Loughborough University , NKF Burbage, Quorn and Shepshed Dynamo.
First Round
| 9th October 2018 | ||
| Anstey Nomads | 2 – 2 (5 – 3 Pens) | Quorn |
| NKF Burbage | 0 – 1 | Barwell |
| Oadby Town | 0 – 1 | Lutterworth Town |
| 16th October 2018 | ||
| Harborough Town | 2 – 9 | Coalville Town |
| Kirby Muxloe | 0 – 1 | St. Andrews |
| Leicester Nirvana | 0 – 3 | Shepshed Dynamo |
| Loughborough University | 2 – 1 | Hinckley AFC |
| 23rd October 2018 | ||
| Leicester Road | 1 – 0 | Loughborough Dynamo |
Quarter Finals
| 11th December 2018 | ||
| Barwell | 0 – 1 | Coalville Town |
| Lutterworth Town | 1 – 1 (3 – 4 Pens) | St. Andrews |
| Shepshed Dynamo | 0 – 0 (3 – 4 Pens) | Leicester Road |
| 15th January 2019 | ||
| Anstey Nomads | 0 – 3 | Loughborough University |
Semi Finals
| 12th February 2019 | ||
| Loughborough University (Midland League – Prem) | 5 – 1 | St. Andrews (United Counties League – Div 1) at Homes Park, Whetstone |
| 19th February 2019 | ||
| Leicester Road (Midland League – Div 1) | 2 – 5 | Coalville Town (Southern League – Prem Central) at Holmes Park, Whetstone |
Final
| 16th April 2019 | ||
| Loughborough University (Midland League – Prem) | 1 – 4 | Coalville Town (Southern League – Prem Central) at Holmes Park, Whetstone |