| Edition | NOC | Athlete | Discipline | Notes | # |
|---|---|---|---|---|---|
| 1976 Summer Olympics |
Cayman Islands
|
? | |||
| 1984 Summer Olympics |
Cayman Islands
|
? | |||
| 1988 Summer Olympics |
Cayman Islands
|
? | |||
| 1992 Summer Olympics |
Cayman Islands
|
? | |||
| 1996 Summer Olympics |
Cayman Islands
|
? | |||
| 2000 Summer Olympics |
Cayman Islands
|
? | |||
| 2004 Summer Olympics |
Cayman Islands
|
Drew MacKay | Swimming | 74 | |
| 2008 Summer Olympics |
Cayman Islands
|
Shaune Fraser | Swimming | 15 | |
| 2010 Winter Olympics |
Cayman Islands
|
Dow Travers | Alpine Skiing | 16 | |
| 2012 Summer Olympics |
Cayman Islands
|
Ronald Forbes | Athletics | 38 | |
| 2014 Winter Olympics |
Cayman Islands
|
Dow Travers | Alpine Skiing | 35 | |
| 2016 Summer Olympics |
Cayman Islands
|
Lara Butler | Swimming | 41 | |
| 2020 Summer Olympics |
Cayman Islands
|
– | OCOG volunteer as flagbearer. | 63 |