| 29 Jul 1986 | Hilda Overy Trophy 1986 | Surrey Young Cricketers v Middlesex Young Cricketers | Kennington Oval, Kennington | |
| 30 Jul 1986 | Hilda Overy Trophy 1986 | Sussex Young Cricketers v Middlesex Young Cricketers | Arundel Castle Cricket Club Ground, Arundel | |
| 31 Jul 1986 | Hilda Overy Trophy 1986 | Buckinghamshire Young Amateurs v Middlesex Young Cricketers | Chalvey Road, Slough | |
| 05 Aug 1986 | Hilda Overy Trophy 1986 | Middlesex Young Cricketers v Young Essex | Old Actonians Sport Club Ground, Ealing | |
| 07 Aug 1986 | Hilda Overy Trophy 1986 | Middlesex Young Cricketers v Hampshire Colts | Ealing | |
| 08 Aug 1986 | Hilda Overy Trophy 1986 | Warwickshire Young Amateurs v Middlesex Young Cricketers | not arranged | |
| 11 Aug 1986 | Hilda Overy Trophy 1986 | Cheshire County Colts v Middlesex Young Cricketers | King's and Selwyn Colleges Ground, Cambridge | |
| 12 Aug 1986 | Hilda Overy Trophy 1986 | Young Essex v Middlesex Young Cricketers | Churchill College Ground, Cambridge | |
| 13 Aug 1986 | Hilda Overy Trophy 1986 | Bedfordshire Colts v Middlesex Young Cricketers | Pembroke College Ground, Cambridge | |
| 14 Aug 1986 | Hilda Overy Trophy 1986 | Cambridgeshire Colts v Middlesex Young Cricketers | Pembroke College Ground, Cambridge | |
| 15 Aug 1986 | Hilda Overy Trophy 1986 | Middlesex Young Cricketers v Norfolk Young Amateurs | Downing College Ground, Cambridge |
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