Most Fifties in a Season for Middlesex
| 5 | OA Shah | 2005 |
| 5 | PR Stirling | 2018 |
| 4 | DJ Malan | 2016 |
| 4 | AB de Villiers | 2019 |
| 4 | SS Eskinazi | 2020 |
| 4 | SS Eskinazi | 2021 |
| 4 | SS Eskinazi | 2023 |
| 4 | SS Eskinazi | 2025 |
| 3 | PR Stirling | 2012 |
| 3 | JL Denly | 2013 |
| 3 | DJ Malan | 2013 |
| 3 | JA Simpson | 2015 |
| 3 | PR Stirling | 2015 |
| 3 | DJ Malan | 2019 |
| 3 | EJG Morgan | 2019 |
| 3 | MDE Holden | 2023 |
| 3 | KS Williamson | 2025 |
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