| 17 Aug 1986 | Final | Leicester Nomads v Market Harborough | Uptonsteel County Ground, Leicester | Results |
| 12 May 1986 | First Round | Ashby Hastings v Loughborough Town | Bath Grounds, Ashby-de-la-Zouch | Results |
| 12 May 1986 | First Round | Barwell v Kirby Muxloe | Kirkby Road, Barwell | Results |
| 12 May 1986 | First Round | Bitteswell v Syston Town | Ullesthorpe Road, Bitteswell | Results |
| 12 May 1986 | First Round | Broughton Astley v Leicester Banks | Recreation Ground, Broughton Astley | Results |
| 12 May 1986 | First Round | Clarendon Park v Stoneygate | Sigiriya Sports Ground, Illston on the Hill | Results |
| 12 May 1986 | First Round | Cropston v Egerton Park | Waterfield Road, Cropston | Results |
| 12 May 1986 | First Round | Hinckley Town v Enderby | Leicester Road, Hinckley | Results |
| 12 May 1986 | First Round | Jones and Shipman v Cosby | not known | Results |
| 12 May 1986 | First Round | Kibworth v Broomleys | Kibworth Cricket Club Ground, Kibworth | Results |
| 12 May 1986 | First Round | Leicester Ivanhoe v Leicester Nomads | Leicester Ivanhoe Cricket Club Ground, Kirby Muxloe | Results |
| 12 May 1986 | First Round | Loughborough Carillon v Leicester Globetrotters | Moor Lane, Loughborough | Results |
| 12 May 1986 | First Round | Lutterworth v Earl Shilton Town | Coventry Road, Lutterworth | Results |
| 12 May 1986 | First Round | Market Harborough v Langtons | Fairfield Road, Market Harborough | Results |
| 12 May 1986 | First Round | Narborough and Littlethorpe v Countesthorpe | Leicester Road, Narborough | Results |
| 12 May 1986 | First Round | Newtown Linford v Electricity Sports | Main Street, Newtown Linford | Results |
| 12 May 1986 | First Round | Old Wyggestonians v Queniborough | Old Wyggestons Ground, Oadby | Results |
| 09 Jun 1986 | Second Round | Leicester Nomads v Cosby | Leicester Nomads, Dog and Gun, Blaby | Results |
| 09 Jun 1986 | Second Round | Hinckley Town v Narborough and Littlethorpe | Leicester Road, Hinckley | Results |
| 09 Jun 1986 | Second Round | not known v Electricity Sports | not known | Results |
| 09 Jun 1986 | Second Round | Clarendon Park v Leicester Globetrotters | not known | Results |
| 09 Jun 1986 | Second Round | Leicester Banks v Syston Town | not known | Results |
| 09 Jun 1986 | Second Round | Lutterworth v Old Wyggestonians | not known | Results |
| 09 Jun 1986 | Second Round | Loughborough Town v Egerton Park | not known | Results |
| 09 Jun 1986 | Second Round | Market Harborough v Broomleys | not known | Results |
| 30 Jun 1986 | Quarter-Final | Lutterworth v Leicester Nomads | Coventry Road, Lutterworth | Results |
| 30 Jun 1986 | Quarter-Final | Syston Town v Clarendon Park | not known | Results |
| 30 Jun 1986 | Quarter-Final | Electricity Sports v Hinckley Town | Aylestone Road, Leicester | Results |
| 30 Jun 1986 | Quarter-Final | Market Harborough v Egerton Park | not known | Results |
| 21 Jul 1986 | Semi-Final | Hinckley Town v Leicester Nomads | Leicester Road, Hinckley | Results |
| 21 Jul 1986 | Semi-Final | Market Harborough v not known | not known | Results |
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