| 23 May 2010 | First Round | Ashby Hastings v Hinckley Town | Bath Grounds, Ashby-de-la-Zouch | Results |
| 23 May 2010 | First Round | Asian Sports v Loughborough Carillon Old Boys | not known | Results |
| 23 May 2010 | First Round | Barkby United v Newtown Linford | Beeby Road, Barkby | Results |
| 23 May 2010 | First Round | Barrow Town v Sileby Town | Nottingham Road, Barrow-on-Soar | Results |
| 30 May 2010 | First Round | Birstall Village v Newbold Verdon | School Lane Playing Fields, Birstall | Results |
| 23 May 2010 | First Round | Broomleys v Kirby Muxloe | Blackwood, Coalville | Results |
| 23 May 2010 | First Round | Cropston v Leicester Banks | Waterfield Road, Cropston | Results |
| 23 May 2010 | First Round | Earl Shilton Town v Loughborough Carillon | Kingscroft Grounds, Earl Shilton | Results |
| 23 May 2010 | First Round | Enderby v Narborough and Littlethorpe | Mill Lane, Enderby | Results |
| 23 May 2010 | First Round | Highfield Rangers v Thorpe Arnold | not known | Results |
| 23 May 2010 | First Round | Kibworth v Kegworth Town | Kibworth Cricket Club New Ground, Kibworth | Results |
| 23 May 2010 | First Round | Lutterworth v Loughborough Town | Coventry Road, Lutterworth | Results |
| 23 May 2010 | First Round | Market Harborough v Leicester Ivanhoe | Fairfield Road, Market Harborough | Results |
| 23 May 2010 | First Round | Countesthorpe v Shree Sanatan Centre | Bassett Avenue, Countesthorpe | Results |
| 23 May 2010 | First Round | Ibstock Town v Stoughton and Thurnby | Coronation Ground, Ibstock | Results |
| 23 May 2010 | First Round | Syston Town v Leicester Caribbeans | Potters Lane, Syston | Results |
| 13 Jun 2010 | Second Round | Barkby United v Stoughton and Thurnby | Beeby Road, Barkby | Results |
| 13 Jun 2010 | Second Round | Broomleys v Loughborough Carillon Old Boys | Blackwood, Coalville | Results |
| 13 Jun 2010 | Second Round | Cropston v Ashby Hastings | Waterfield Road, Cropston | Results |
| 20 Jun 2010 | Second Round | Loughborough Town v Shree Sanatan Centre | Park Road, Loughborough | Results |
| 13 Jun 2010 | Second Round | Market Harborough v Newbold Verdon | Fairfield Road, Market Harborough | Results |
| 13 Jun 2010 | Second Round | Narborough and Littlethorpe v Highfield Rangers | Leicester Road, Narborough | Results |
| 13 Jun 2010 | Second Round | Sileby Town v Earl Shilton Town | Mill Lane, Sileby | Results |
| 13 Jun 2010 | Second Round | Syston Town v Kibworth | Potters Lane, Syston | Results |
| 11 Jul 2010 | Quarter-Final | Broomleys v Market Harborough | Blackwood, Coalville | Results |
| 11 Jul 2010 | Quarter-Final | Cropston v Highfield Rangers | Waterfield Road, Cropston | Results |
| 11 Jul 2010 | Quarter-Final | Sileby Town v Kibworth | Mill Lane, Sileby | Results |
| 18 Jul 2010 | Quarter-Final | Barkby United v Loughborough Town | Beeby Road, Barkby | Results |
| 08 Aug 2010 | Semi-Final | Loughborough Town v Sileby Town | Park Road, Loughborough | Results |
| 08 Aug 2010 | Semi-Final | Market Harborough v Cropston | Fairfield Road, Market Harborough | Results |
| 12 Sep 2010 | Final | Loughborough Town v Market Harborough | Uptonsteel County Ground, Leicester | Results |
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