| 1984 Summer Olympics |
Cayman Islands
|
Carson Ebanks |
Sailing |
|
|
| 1988 Summer Olympics |
Cayman Islands
|
Alfred Ebanks |
Cycling Road |
|
|
| 1996 Summer Olympics |
Cayman Islands
|
Carson Ebanks |
Sailing |
|
|
| 2000 Summer Olympics |
Cayman Islands
|
Kareem Streete-Thompson |
Athletics |
|
36 |
| 2004 Summer Olympics |
Cayman Islands
|
Cydonie Mothersill |
Athletics |
|
74 |
| 2008 Summer Olympics |
Cayman Islands
|
Ronald Forbes |
Athletics |
|
15 |
| 2010 Summer Youth Olympics |
Cayman Islands
|
Seiji Groome |
Swimming |
|
38 |
| 2010 Winter Olympics |
Cayman Islands
|
Dow Travers |
Alpine Skiing |
|
16 |
| 2012 Summer Olympics |
Cayman Islands
|
Kemar Hyman |
Athletics |
|
38 |
| 2012 Winter Youth Olympics |
Cayman Islands
|
Dean Travers |
Alpine Skiing |
|
27 |
| 2014 Summer Youth Olympics |
Cayman Islands
|
Florence Allan |
Sailing |
|
35 |
| 2014 Winter Olympics |
Cayman Islands
|
Dow Travers |
Alpine Skiing |
|
34 |
| 2016 Summer Olympics |
Cayman Islands
|
Ronald Forbes |
Athletics |
|
41 |
| 2018 Summer Youth Olympics |
Cayman Islands
|
Jordan Crooks |
Swimming |
|
34 |
| 2020 Summer Olympics |
Cayman Islands
|
Jillian Crooks |
Swimming |
|
63 |
| 2020 Summer Olympics |
Cayman Islands
|
Brett Fraser |
Swimming |
|
63 |
| 2024 Summer Olympics |
Cayman Islands
|
Charlotte Webster |
Sailing |
|
36 |
| 2024 Summer Olympics |
Cayman Islands
|
Jordan Crooks |
Swimming |
|
36 |