| 25 Jul 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Buckinghamshire Young Amateurs | not arranged | |
| 02 Aug 1989 | Hilda Overy Trophy 1989 | Sussex Young Cricketers v Middlesex Young Cricketers | Arundel Castle Cricket Club Ground, Arundel | |
| 03 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Association of Kent Cricket Clubs Under-19s | not arranged | |
| 04 Aug 1989 | Hilda Overy Trophy 1989 | Hampshire Colts v Middlesex Young Cricketers | Dean Park, Bournemouth | |
| 08 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Young Essex | not arranged | |
| 09 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Surrey Young Cricketers | not arranged | |
| 11 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Warwickshire Cricket Association Under-19s | Durrants Sports Ground, Croxley Green | |
| 14 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Norfolk Young Cricketers | Pembroke College Ground, Cambridge | |
| 15 Aug 1989 | Hilda Overy Trophy 1989 | Leicestershire Young Cricketers v Middlesex Young Cricketers | Emmanuel College Ground, Cambridge | |
| 16 Aug 1989 | Hilda Overy Trophy 1989 | Lincolnshire Colts v Middlesex Young Cricketers | FP Fenner's Ground, Cambridge | Lost by 63 runs |
| 17 Aug 1989 | Hilda Overy Trophy 1989 | Middlesex Young Cricketers v Suffolk Colts | Churchill College Ground, Cambridge | |
| 18 Aug 1989 | Hilda Overy Trophy 1989 | Huntingdonshire and Peterborough County Cricket Association Colts v Middlesex Young Cricketers | Downing College Ground, Cambridge |
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