| 27 May 1999 | ECB 38-County Cup 1999 | Surrey Cricket Board v Middlesex Cricket Board | Imber Court, East Molesey | Lost by 9 wkts |
| 13 Jun 1999 | ECB 38-County Cup 1999 | Hertfordshire v Middlesex Cricket Board | Denis Compton Oval, Shenley | Lost by 55 runs |
| 17 Jun 1999 | ECB 38-County Cup 1999 | Middlesex Cricket Board v Bedfordshire | Old Deer Park, Richmond | Won by 92 runs |
| 27 Jun 1999 | ECB 38-County Cup 1999 | Bedfordshire v Middlesex Cricket Board | Lancot Park, Totternhoe | Lost on faster scoring rate |
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