| 18 May 1999 | ECB Over-50s County Championship 1999 | Middlesex Over-50s v Isle of Wight Over-50s | Corfton Road, Ealing | |
| 01 Jun 1999 | ECB Over-50s County Championship 1999 | Middlesex Over-50s v Sussex Over-50s | Lincoln Road, Enfield | |
| 16 Jun 1999 | ECB Over-50s County Championship 1999 | Hampshire Over-50s v Middlesex Over-50s | Privett Park, Gosport | |
| 23 Jun 1999 | ECB Over-50s County Championship 1999 | Suffolk Over-50s v Middlesex Over-50s | The Meadow, Hadleigh | |
| 29 Jun 1999 | ECB Over-50s County Championship 1999 | Kent Over-50s v Middlesex Over-50s | Bat and Ball Ground, Gravesend | |
| 06 Jul 1999 | ECB Over-50s County Championship 1999 | Middlesex Over-50s v Surrey Over-50s | Uxbridge Cricket Club Ground, Uxbridge | |
| 14 Jul 1999 | ECB Over-50s County Championship 1999 | Essex Over-50s v Middlesex Over-50s | Gidea Park Sports Ground, Romford | |
| 01 Aug 1999 | ECB Over-50s County Championship 1999 | Wales Over-50s v Middlesex Over-50s | not arranged |
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