| Date | Competition | Outcome | Home team | Score/Time | Visiting Team | ||
|---|---|---|---|---|---|---|---|
| 06/03/1995 | Olympi… | W |
Antigua an… | 1 - 2 | Cayman Isla… | More info | |
| 06/05/1995 | Olympi… | L |
Cayman Isla… | 0 - 4 | St. Lucia U23 | More info | |
| 06/07/1995 | Olympi… | L |
Jamaica U23 | 7 - 0 | Cayman Isla… | More info | |
| 09/05/2003 | Olympi… | L |
Grenada U23 | 5 - 0 | Cayman Isla… | More info | |
| 10/11/2003 | Olympi… | L |
Cayman Isla… | 1 - 5 | Grenada U23 | More info | |
| 09/08/2007 | Olympi… | L |
Puerto Rico U23 | 4 - 1 | Cayman Isla… | More info | |
| 09/10/2007 | Olympi… | D |
Cayman Isla… | 0 - 0 | Bermuda U23 | More info | |
| 09/12/2007 | Olympi… | L |
Cuba U23 | 6 - 0 | Cayman Isla… | More info | |
| 08/03/2011 | Olympi… | L |
Suriname U23 | 5 - 0 | Cayman Isla… | View events | More info |
| 08/05/2011 | Olympi… | L |
Jamaica U23 | 1 - 0 | Cayman Isla… | View events | More info |
| 08/07/2011 | Olympi… | L |
Cayman Isla… | 0 - 2 | St. Vincen… | View events | More info |