| 02 Apr 2020 | Marylebone Cricket Club University matches 2020 | Middlesex v Cambridge Marylebone Cricket Club University | Merchant Taylors' School Ground, Northwood | Cancelled |
| 01 Aug 2020 | Bob Willis Trophy 2020 | Surrey v Middlesex | The Kia Oval, Kennington | Won by 190 runs |
| 08 Aug 2020 | Bob Willis Trophy 2020 | Middlesex v Hampshire | Brunton Memorial Ground, Radlett | Lost by 3 wkts |
| 15 Aug 2020 | Bob Willis Trophy 2020 | Kent v Middlesex | Spitfire Ground, St Lawrence, Canterbury | Drawn |
| 22 Aug 2020 | Bob Willis Trophy 2020 | Middlesex v Sussex | Brunton Memorial Ground, Radlett | Won by 5 wkts |
| 06 Sep 2020 | Bob Willis Trophy 2020 | Essex v Middlesex | The Cloudfm County Ground, Chelmsford | Lost by 9 wkts |
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