| 18 May 2014 | Preliminary Round | Newbold Verdon v Narborough and Littlethorpe | Way Playing Field, Newbold Verdon | Results |
| 18 May 2014 | Preliminary Round | Broomleys v Leicester Ivanhoe | Blackwood, Coalville | Results |
| 18 May 2014 | Preliminary Round | Shree Sanatan Centre v Market Harborough | Upper Broughton, Melton Mowbray | Results |
| 18 May 2014 | Preliminary Round | Kirby Muxloe v Leicester Caribbeans | Ratby Lane, Kirby Muxloe | Results |
| 15 Jun 2014 | First Round | Blaby Village v Huncote | Northfield Park, Blaby | Results |
| 15 Jun 2014 | First Round | Lutterworth v Maher Stars | Coventry Road, Lutterworth | Results |
| 15 Jun 2014 | First Round | Electricity Sports v Market Harborough | Aylestone Road, Leicester | Results |
| 15 Jun 2014 | First Round | Cropston v Leicester Ivanhoe | Waterfield Road, Cropston | Results |
| 15 Jun 2014 | First Round | Highfield Rangers v Sileby Town | Gleneagles Avenue, Leicester | Results |
| 15 Jun 2014 | First Round | Asian Sports v Leicester Banks | School Lane Playing Fields, Birstall | Results |
| 15 Jun 2014 | First Round | Loughborough University Staff v Earl Shilton Town | Brockington Ground, Loughborough | Results |
| 15 Jun 2014 | First Round | Thorpe Arnold v Burbage | Waltham Road, Thorpe Arnold | Results |
| 15 Jun 2014 | First Round | Hinckley Town v Narborough and Littlethorpe | Leicester Road, Hinckley | Results |
| 15 Jun 2014 | First Round | Barrow Town v Enderby | Nottingham Road, Barrow-on-Soar | Results |
| 15 Jun 2014 | First Round | Loughborough Outwoods v Kegworth Town | Nanpantan Sports Ground, Loughborough | Results |
| 15 Jun 2014 | First Round | Ibstock Town v Leicestershire University Staff | Coronation Ground, Ibstock | Results |
| 15 Jun 2014 | First Round | Loughborough Town v Leicester Caribbeans | Park Road, Loughborough | Results |
| 15 Jun 2014 | First Round | Barkby United v Stoughton and Thurnby | Beeby Road, Barkby | Results |
| 15 Jun 2014 | First Round | Syston Town v Hinckley Amateur | Potters Lane, Syston | Results |
| 15 Jun 2014 | First Round | Ashby Hastings v Kibworth | Bath Grounds, Ashby-de-la-Zouch | Results |
| 06 Jul 2014 | Second Round | Lutterworth v Kibworth | Coventry Road, Lutterworth | Results |
| 06 Jul 2014 | Second Round | Sileby Town v Barkby United | Mill Lane, Sileby | Results |
| 06 Jul 2014 | Second Round | Thorpe Arnold v Cropston | Waltham Road, Thorpe Arnold | Results |
| 06 Jul 2014 | Second Round | Loughborough Town v Leicester Banks | Park Road, Loughborough | Results |
| 06 Jul 2014 | Second Round | Enderby v Huncote | Mill Lane, Enderby | Results |
| 06 Jul 2014 | Second Round | Market Harborough v Earl Shilton Town | Fairfield Road, Market Harborough | Results |
| 06 Jul 2014 | Second Round | Hinckley Town v Kegworth Town | Leicester Road, Hinckley | Results |
| 06 Jul 2014 | Second Round | Ibstock Town v Syston Town | Coronation Ground, Ibstock | Results |
| 27 Jul 2014 | Quarter-Final | Enderby v Ibstock Town | Mill Lane, Enderby | Results |
| 27 Jul 2014 | Quarter-Final | Market Harborough v Loughborough Town | Fairfield Road, Market Harborough | Results |
| 27 Jul 2014 | Quarter-Final | Lutterworth v Sileby Town | Coventry Road, Lutterworth | Results |
| 27 Jul 2014 | Quarter-Final | Hinckley Town v Cropston | Leicester Road, Hinckley | Results |
| 17 Aug 2014 | Semi-Final | Sileby Town v Ibstock Town | Mill Lane, Sileby | Results |
| 17 Aug 2014 | Semi-Final | not known v not known | not arranged | Results |
| 07 Sep 2014 | Final | Hinckley Town v Sileby Town | Uptonsteel County Ground, Leicester | Results |
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