Westerby Challenge Cup 2008/09
Barwell beat Quorn in the final.
Due to the creation of the East Midlands Counties League, the Challenge Cup was expanded for this season to 19 teams, which required the addition of a second round. The competition went back to the more familiar 12 team format for next season.
First Round > Second Round > Quarter Finals > Semi Finals > Final
Entries – 19 Teams
Football Conference (1 team)
Hinckley United.
Northern Premier League (3 teams)
Loughborough Dynamo, Quorn and Shepshed Dynamo.
Midland Football Alliance (4 teams)
Barwell , Coalville Town, Friar Lane & Epworth and Oadby Town.
East Midlands Counties League (8 teams)
Bardon Hill Sports, Barrow Town, Ellistown, Hinckley Downes, Holwell Sports, Ibstock United, Kirby Muxloe and St. Andrews.
Midland Football Combination (2 teams)
Heather St. John’s and Loughborough University.
Leicestershire Senior League (1 team)
Blaby & Whetstone Athletic.
First Round
| 14th October 2008 | ||
| Bardon Hill Sports | 2 – 5 (aet) | Barrow Town |
| Ibstock United | 1 – 3 | Barwell |
| St. Andrews | 4 – 0 | Kirby Muxloe |
Byes: Blaby & Whetstone Athletic, Coalville Town, Ellistown, Friar Lane & Epworth, Heather St. John’s, Hinckley Downes, Hinckley United, Holwell Sports, Loughborough Dynamo, Loughborough University, Oadby Town, Quorn and Shepshed Dynamo.
Second Round
| 4th November 2008 | ||
| Coalville Town | 4 – 0 | Friar Lane & Epworth |
| Hinckley Downes | 2 – 3 | Loughborough Dynamo |
| Quorn | 7 – 2 | Blaby & Whetstone Athletic |
| 11th November 2008 | ||
| Barrow Town | 6 – 1 | Ellistown |
| Barwell | 4 – 1 | St. Andrews |
| Heather St. John’s | 2 – 1 | Holwell Sports |
| Loughborough University | 3 – 2 | Oadby Town |
| 15th December 2008 | ||
| Hinckley United | 2 – 3 | Shepshed Dynamo |
Quarter Finals
| 9th December 2008 | ||
| Barrow Town | 0 – 1 | Barwell |
| Coalville Town | 3 – 1 | Heather St. John’s |
| 13th January 2009 | ||
| Quorn | 2 – 1 | Loughborough University |
| 24th February 2009 | ||
| Shepshed Dynamo | 4 – 2 (aet) | Loughborough Dynamo |
Semi Finals
| Date Unknown | ||
| Barwell (Midland Football Alliance) | 0 – 2 (abandoned at half time) | Coalville Town (Midland Football Alliance) at Holmes Park, Whetstone. |
| 16th March 2010 | ||
| Shepshed Dynamo (Northern Premier League – Div 1 South) | 0 – 1 | Quorn (Northern Premier League – Div 1 South) at Holmes Park, Whetstone. |
Replay
| 27th April 2009 | ||
| Barwell (Midland Football Alliance) | 3 – 2 (aet) | Coalville Town (Midland Football Alliance) at Holmes Park, Whetstone. |
Final
| 13th May 2009 | ||
| Barwell (Midland Football Alliance) | 2 – 0 | Quorn (Northern Premier League – Div 1 South) at Walkers Stadium, Leicester |