| 19 Aug 1969 | Hilda Overy Trophy 1969 | Essex Young Amateurs v Middlesex Young Cricketers | Gidea Park Sports Ground, Romford | |
| 25 Aug 1969 | Hilda Overy Trophy 1969 | Middlesex Young Cricketers v Buckinghamshire Young Amateurs | Tentelow Lane, Osterley | |
| 26 Aug 1969 | Hilda Overy Trophy 1969 | Association of Kent Cricket Clubs Under-19s v Middlesex Young Cricketers | Foxgrove Road, Beckenham | |
| 01 Sep 1969 | Hilda Overy Trophy 1969 | Surrey Young Cricketers v Middlesex Young Cricketers | National Westminster Bank Sports Ground, Norbury | Drawn |
| 04 Sep 1969 | Hilda Overy Trophy 1969 | Middlesex Young Cricketers v Sussex Young Cricketers | Ealing |
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