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Cayman Islands |  1  1  0
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| 2011 | 2012 | 2013 | 2014 | 2015 | 2016 | 2017 | 2018 | 2019 | 2020 | 2021 | 2022 | 2023 | 2024 |
| Contest | Player | Artist / Song | F | SF | QF | ||
|---|---|---|---|---|---|---|---|
 1: New York
|
Pooley | Keisha Buchanan | 2nd | 1st | 3rd | ||
| "Fearless" | 91 | 90 | 83 | ||||
 2: São Paulo
|
Pooley | Natalia Kills | 1st | 2nd | |||
| "Wonderland" | 67 | 95 | |||||
| Key | |||||||
|---|---|---|---|---|---|---|---|
| 1st | 2nd | 3rd | Finalist | Qualified | Wildcard / AC | Last | Disqualified |
| * Deducted points for failing to vote | |||||||