| 21 May 1986 | Preliminary Round | Hertfordshire Cricket League v Middlesex County Cricket League | not known | Results |
| 21 May 1986 | Preliminary Round | Middlesex Cricket League v Morrant Essex Cricket League | not known | Results |
| 28 May 1986 | Preliminary Round | Cambridgeshire Premier Cricket League v Essex Cricket League | Papworth Cricket Club Ground, Papworth Everard | Results |
| 28 May 1986 | Preliminary Round | Chilterns Cricket League v 1975 Cricket League | not known | Results |
| 21 May 1986 | Preliminary Round | Home Counties Cricket League v Hertfordshire Cricket Competition | not known | Results |
| 21 May 1986 | Preliminary Round | Southern Cricket League v Arun Valley Cricket League | Kinson Park Road, Bournemouth | Results |
| 21 May 1986 | Preliminary Round | North Kent Cricket League v Surrey County Cricket League | not known | Results |
| 21 May 1986 | Preliminary Round | Kent Intermediate Cricket League v Sussex Championship | not known | Results |
| 21 May 1986 | Preliminary Round | East Kent Cricket League v Surrey Cricketers League | not known | Results |
| 21 May 1986 | Preliminary Round | South East Cricket League v Surrey Championship | not known | Results |
| 11 Jun 1986 | First Round | Berkshire County Cricket League v Essex Cricket League | Gallowstree Common, Kidmore End | Results |
| 11 Jun 1986 | First Round | Essex Suburban Cricket Alliance v Trinity Cricket League | not known | Results |
| 11 Jun 1986 | First Round | Hertfordshire Cricket Competition v Eastern Cricket League | not known | Results |
| 11 Jun 1986 | First Round | Cherwell Cricket League v Middlesex Cricketers League | not known | Results |
| 11 Jun 1986 | First Round | West Middlesex Cricket League v Kent Metropolitan Cricket League | St Bernard's Hospital Ground, Ealing | Results |
| 11 Jun 1986 | First Round | Essex County Cricket League v Thames Valley Cricket League | Port of London Authority Ground, Ilford | Results |
| 11 Jun 1986 | First Round | 1982 Cricket League v Hertfordshire Cricket League | Manor Park Grounds, Acton | Results |
| 11 Jun 1986 | First Round | 1975 Cricket League v Morrant Essex Cricket League | Woods Cricket Ground, Harefield | Results |
| 11 Jun 1986 | First Round | Sussex Cricket League v South London Community Cricket League | not known | Results |
| 11 Jun 1986 | First Round | Wey Valley Cricket League v Southern Cricket League | Memorial Fields, Ottershaw | Results |
| 11 Jun 1986 | First Round | Mid-Kent Cricket League v Sussex Invitation Cricket League | not known | Results |
| 11 Jun 1986 | First Round | East Sussex Cricket League v Surrey Cricket League | The Recreation Ground, Glynde | Results |
| 11 Jun 1986 | First Round | East Kent Cricket League v Three Counties Cricket League | not known | Results |
| 11 Jun 1986 | First Round | South Thames Cricket League v Kent Intermediate Cricket League | Goddington Dene, Orpington | Results |
| 11 Jun 1986 | First Round | Kent Cricket League v Surrey County Cricket League | not known | Results |
| 11 Jun 1986 | First Round | Thameside Cricket League v Surrey Championship | not known | Results |
| 02 Jul 1986 | Second Round | Thames Valley Cricket League v Essex Cricket League | Church Road, Reading | Results |
| 02 Jul 1986 | Second Round | Essex Suburban Cricket Alliance v Middlesex Cricketers League | not known | Results |
| 02 Jul 1986 | Second Round | Hertfordshire Cricket League v Hertfordshire Cricket Competition | Ditchmore Lane, Stevenage | Results |
| 02 Jul 1986 | Second Round | 1975 Cricket League v Kent Metropolitan Cricket League | Woods Cricket Ground, Harefield | Results |
| 02 Jul 1986 | Second Round | Southern Cricket League v Surrey Cricket League | not known | Results |
| 02 Jul 1986 | Second Round | South Thames Cricket League v Mid-Kent Cricket League | National Westminster Bank Sports Ground, Beckenham | Results |
| 02 Jul 1986 | Second Round | East Kent Cricket League v Kent Cricket League | not known | Results |
| 02 Jul 1986 | Second Round | Sussex Cricket League v Surrey Championship | Recreation Ground, Haywards Heath | Results |
| 23 Jul 1986 | Quarter-Final | East Kent Cricket League v Hertfordshire Cricket League | Bottles Lane, Rodmersham Green | Results |
| 23 Jul 1986 | Quarter-Final | Middlesex Cricketers League v Sussex Cricket League | not known | Results |
| 23 Jul 1986 | Quarter-Final | Essex Cricket League v Southern Cricket League | Overton Drive, Wanstead | Results |
| 23 Jul 1986 | Quarter-Final | South Thames Cricket League v 1975 Cricket League | Commercial Union Assurance Company Ground, Beckenham | Results |
| 13 Aug 1986 | Semi-Final | South Thames Cricket League v Middlesex Cricketers League | National Westminster Bank Sports Ground, Norbury | Results |
| 13 Aug 1986 | Semi-Final | Hertfordshire Cricket League v Southern Cricket League | Clarence Park, St Albans | Results |
| 10 Sep 1986 | Final | Middlesex Cricketers League v Hertfordshire Cricket League | The Paulin Ground, Winchmore Hill | Results |
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