Champion
| Season | Team | Title | |
|---|---|---|---|
| 2021 |  | Scholars International | 13. |
| 2020 |  | Bodden Town FC | 4. |
| 2019 | | Scholars International | 12. |
| 2018 | | Scholars International | 11. |
| 2017 | | Bodden Town FC | 3. |
| 2016 | | Scholars International | 10. |
| 2015 | | Scholars International | 9. |
Cayman Islands League