| 25 May 2008 | Under-15 County Cup 2008 | Suffolk Under-15s v Middlesex Under-15s | Ipswich School Ground, Ipswich | Cancelled |
| 15 Jun 2008 | Under-15 County Cup 2008 | Essex Under-15s v Middlesex Under-15s | Garon Park, Southend-on-Sea | Won by 5 wkts |
| 22 Jun 2008 | Under-15 County Cup 2008 | Middlesex Under-15s v Buckinghamshire Under-15s | not arranged | Won by 9 wkts |
| 29 Jun 2008 | Under-15 County Cup 2008 | Middlesex Under-15s v Bedfordshire Under-15s | The John Lyon School Ground, Harrow-on-the-Hill | Won by 8 wkts |
| 10 Aug 2008 | Under-15 County Cup 2008 | Kent Under-15s v Middlesex Under-15s | The Kent County Cricket Ground, Beckenham | Won by 3 wkts |
| 23 Aug 2008 | Under-15 County Cup 2008 | Derbyshire Under-15s v Middlesex Under-15s | Oundle School Ground, Oundle | Won by 4 wkts |
| 24 Aug 2008 | Under-15 County Cup 2008 | Devon Under-15s v Middlesex Under-15s | Oundle School Ground, Oundle | Won by 1 run |
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