| 14 May 2014 | ECB Over-50s County Championship 2014 | Surrey Over-50s v Middlesex Over-50s | Master Park, Oxted | Lost by 48 runs |
| 21 May 2014 | ECB Over-50s County Championship 2014 | Middlesex Over-50s v Berkshire Over-50s | not arranged | Won by 4 wkts |
| 04 Jun 2014 | ECB Over-50s County Championship 2014 | Middlesex Over-50s v Kent Over-50s | Stanmore Common, Stanmore | Cancelled |
| 11 Jun 2014 | ECB Over-50s County Championship 2014 | Middlesex Over-50s v Essex Over-50s | Harrow Recreation Ground, Harrow | Lost by 2 wkts |
| 18 Jun 2014 | ECB Over-50s County Championship 2014 | Buckinghamshire Over-50s v Middlesex Over-50s | Rectory Field, Farnham Royal | Won by 67 runs |
| 02 Jul 2014 | ECB Over-50s County Championship 2014 | Sussex Over-50s v Middlesex Over-50s | Spen Cama Memorial Ground, Fulking | Lost by 65 runs |
| 09 Jul 2014 | ECB Over-50s County Championship 2014 | Middlesex Over-50s v Hertfordshire Over-50s | The Paulin Ground, Winchmore Hill | Lost by 5 wkts |
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