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| Time | Date | Name | Team | Meet |
|---|---|---|---|---|
| 27.72 | Dec. 16, 2023 | Will Sellars | Cayman Islands Swimming Federation | ASAJ Christmas Open |
| 27.81 | April 20, 2019 | Jordan Crooks | Cayman Islands Swimming Federation | XXXIV Carifta Swimming Championships |
| 28.48 | June 30, 2018 | Jordan Crooks | Cayman Islands Swimming Federation | XXXI CCCAN Swimming Championships |
| 28.81 | March 31, 2018 | Zachary Moore | Cayman Islands Swimming Federation | CARIFTA Swimming Championships |
| 29.17 | July 30, 2014 | Cole Morgan | Cayman Islands Swimming Federation | Speedo Champions Series - Orlando |
| 29.39 | April 22, 2014 | Cole Morgan | Cayman Islands Swimming Federation | CARIFTA Swimming Championships |
| 29.52 | Jan. 13, 2007 | Brett Fraser | Cayman Stingray Swim Club | SYS SR CIRCUIT |