| 02 Jun 2006 | Under-14 County Cup 2006 | Middlesex Under-14s v Essex Under-14s | Lincoln Road, Enfield | Won by 49 runs |
| 04 Jun 2006 | Under-14 County Cup 2006 | Buckinghamshire Under-14s v Middlesex Under-14s | The Memorial Ground, Burnham | Won by 82 runs |
| 15 Jun 2006 | Under-14 County Cup 2006 | Bedfordshire Under-14s v Middlesex Under-14s | The Pyghties, Henlow | Won by 3 runs |
| 18 Jun 2006 | Under-14 County Cup 2006 | Middlesex Under-14s v Suffolk Under-14s | The John Lyon School Ground, Harrow-on-the-Hill | Won by 122 runs |
| 19 Jul 2006 | Under-14 County Cup 2006 | Kent Under-14s v Middlesex Under-14s | Polo Farm Sports Club, Canterbury | Won by 1 run |
| 14 Aug 2006 | Under-14 County Cup 2006 | Middlesex Under-14s v Wales Under-14s | Oundle School Ground, Oundle | Lost by 83 runs |
| 15 Aug 2006 | Under-14 County Cup 2006 | Cheshire Under-14s v Middlesex Under-14s | Oundle School Ground, Oundle | Lost by 6 wkts |
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