| 02 Jun 2021 | ECB Over-50 County Championship 2021 | Surrey Over-50s v Middlesex Over-50s | Cheam Road, Sutton | Lost by 45 runs |
| 09 Jun 2021 | ECB Over-50 County Championship 2021 | Buckinghamshire Over-50s v Middlesex Over-50s | Rectory Field, Farnham Royal | Won by 6 wkts |
| 23 Jun 2021 | ECB Over-50 County Championship 2021 | Middlesex Over-50s v Hertfordshire Over-50s | Harrow Recreation Ground, Harrow | Lost by 39 runs |
| 30 Jun 2021 | ECB Over-50 County Championship 2021 | Middlesex Over-50s v Essex Over-50s | not arranged | Won by 3 wkts |
| 14 Jul 2021 | ECB Over-50 County Championship 2021 | Sussex Over-50s v Middlesex Over-50s | Spen Cama Memorial Ground, Fulking | Lost by 6 wkts |
| 21 Jul 2021 | ECB Over-50 County Championship 2021 | Middlesex Over-50s v Kent Over-50s | Harrow Recreation Ground, Harrow | Won by 9 wkts |
| 01 Aug 2021 | ECB Over-50 County Championship 2021 | Middlesex Over-50s v Berkshire Over-50s | The Paulin Ground, Winchmore Hill | Lost by 2 runs |
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