Challenge Cup
- Official Website – https://www.leicestershirefa.com/county-cups
The Leicestershire Challenge Cup is the top county cup competition in Leicestershire. It is currently open to all teams higher than step 7 in the non-league pyramid but in past seasons it also included invited teams from the Leicestershire Senior League.
It was first played in the 1950/51 season and during the early years was invitation only and consisted of a small number of teams.
Since the 1991/92 season the Challenge Cup has been sponsored by Westerby Investment Management and is known as the Westerby Challenge Cup or Westerby Cup.
| Winners | Runners Up | |
|---|---|---|
| 1950/51 | Leicester City | Brush Sports |
| 1951/52 | Leicester City | Brush Sports |
| 1952/53 | Leicester City | Brush Sports |
| 1953/54 | Leicester City | Brush Sports |
| 1954/55 | Leicester City | Hinckley Athletic |
| 1955/56 | Leicester City | Hinckley Athletic |
| 1956/57 | Leicester City | Anstey Nomads |
| 1957/58 | Hinckley Athletic | Brush Sports |
| 1958/59 | Hinckley Athletic | Anstey Nomads |
| 1959/60 | Hinckley Athletic | Atherstone Town |
| 1960/61 | Hinckley Athletic | Loughborough United |
| 1961/62 | Hinckley Athletic | Loughborough Colleges |
| 1962/63 | Loughborough Colleges | Loughborough United |
| 1963/64 | Loughborough United | Hinckley Athletic |
| 1964/65 | Hinckley Athletic | Oadby Town |
| 1965/66 | Loughborough United | Hinckley Athletic |
| 1966/67 | Loughborough United | Measham Social Welfare |
| 1967/68 | Hinckley Athletic | Oadby Town |
| 1968/69 | Oadby Town | Enderby Town |
| 1969/70 | Newfoundpool WMC | Loughborough United |
| 1970/71 | Oadby Town | Enderby Town |
| 1971/72 | Friar Lane Old Boys | Oadby Town |
| 1972/73 | Enderby Town | Anstey Nomads |
| 1973/74 | Friar Lane Old Boys | Oadby Town |
| 1974/75 | Friar Lane Old Boys | Enderby Town |
| 1975/76 | Enderby Town | Jones & Shipman |
| 1976/77 | Friar Lane Old Boys | Oadby Town |
| 1977/78 | Anstey Nomads | Oadby Town |
| 1978/79 | Enderby Town | Anstey Nomads |
| 1979/80 | Enderby Town | Anstey Nomads |
| 1980/81 | Wigston Fields | Oadby Town |
| 1981/82 | Shepshed Charterhouse | Oadby Town |
| 1982/83 | Leicester City | Enderby Town |
| 1983/84 | Wigston Fields | Anstey Nomads |
| 1984/85 | Wigston Fields | Hinckley Athletic |
| 1985/86 | Shepshed Charterhouse | Leicester United |
| 1986/87 | Leicester United | Birstall United |
| 1987/88 | Leicester United | Wigston Fields |
| 1988/89 | Leicester City | Leicester United |
| 1989/90 | Hinckley Town | Shepshed Charterhouse |
| 1990/91 | Leicester City | Hinckley Town |
| 1991/92 | Leicester City | Leicester United |
| 1992/93 | Shepshed Albion | Leicester City |
| 1993/94 | Leicester City | Hinckley Town |
| 1994/95 | Leicester City | Hinckley Town |
| 1995/96 | Leicester City | St. Andrews |
| 1996/97 | St. Andrews | Shepshed Dynamo |
| 1997/98 | Leicester City | Shepshed Dynamo |
| 1998/99 | Leicester City | Oadby Town |
| 1999/00 | Leicester City | Barwell |
| 2000/01 | Hinckley United | Barwell |
| 2001/02 | Hinckley United | Oadby Town |
| 2002/03 | Leicester City | Shepshed Dynamo |
| 2003/04 | Hinckley United | Oadby Town |
| 2004/05 | Oadby Town | Barwell |
| 2005/06 | Leicester City | Coalville Town |
| 2006/07 | Hinckley United | Barwell |
| 2007/08 | Oadby Town | Friar Lane & Epworth |
| 2008/09 | Barwell | Quorn |
| 2009/10 | Loughborough Dynamo | Barwell |
| 2010/11 | Quorn | Hinckley United |
| 2011/12 | Loughborough Dynamo | Hinckley United |
| 2012/13 | Coalville Town | Loughborough Dynamo |
| 2013/14 | Blaby & Whetstone Athletic | Quorn |
| 2014/15 | Barwell | Coalville Town |
| 2015/16 | Leicester Nirvana | Barwell |
| 2016/17 | Barwell | Coalville Town |
| 2017/18 | Coalville Town | Loughborough Dynamo |
| 2018/19 | Coalville Town | Loughborough University |
| 2019/20 | final not played | |
| 2020/21 | no competition | |
| 2021/22 | no competition | |
| 2022/23 | no competition | |
| 2023/24 | Anstey Nomads | Loughborough Students |
| 2024/25 | Anstey Nomads | Loughborough Students |