| 30 May 2021 | Royal London Under-14 County Cup 2021 | Middlesex Under-14s v Essex Under-14s | not arranged | Won by 6 wkts |
| 13 Jun 2021 | Royal London Under-14 County Cup 2021 | Middlesex Under-14s v Surrey Under-14s | Merchant Taylors' School Ground, Northwood | Won by 43 runs |
| 20 Jun 2021 | Royal London Under-14 County Cup 2021 | Middlesex Under-14s v Kent Under-14s | not arranged | Lost by 87 runs |
| 04 Jul 2021 | Royal London Under-14 County Cup 2021 | Essex Under-14s v Middlesex Under-14s | Garon Park, Southend-on-Sea | Lost by 9 runs |
| 11 Jul 2021 | Royal London Under-14 County Cup 2021 | Surrey Under-14s v Middlesex Under-14s | not arranged | Lost by 60 runs |
| 25 Jul 2021 | Royal London Under-14 County Cup 2021 | Middlesex Under-14s v Sussex Under-14s | Merchant Taylors' School Ground, Northwood | Won by 7 wkts |
| 15 Aug 2021 | Royal London Under-14 County Cup 2021 | Kent Under-14s v Middlesex Under-14s | Three Hills Sports Park, Folkestone | Won by 4 wkts |
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