| 29.07.2019 | CNCF OLQ | Haiti U23 | 2-2 | Cayman Islands U23 | ![]() |
| 25.07.2019 | CNCF OLQ | Cayman Islands U23 | 0-1 | Grenada U23 | ![]() |
| 28.06.2015 | CNCF OLQ | Barbados U23 | 1-0 | Cayman Islands U23 | ![]() |
| 27.06.2015 | CNCF OLQ | Haiti U23 | 4-0 | Cayman Islands U23 | ![]() |
| 24.06.2015 | CNCF OLQ | Cayman Islands U23 | 0-6 | St Kitts & Nevis U23 | ![]() |
| 07.08.2011 | CNCF OLQ | Cayman Islands U23 | 0-2 | St Vincent/Grenadines U23 | ![]() |
| 05.08.2011 | CNCF OLQ | Jamaica U23 | 1-0 | Cayman Islands U23 | ![]() |
| 03.08.2011 | CNCF OLQ | Suriname U23 | 5-0 | Cayman Islands U23 | ![]() |
| 13.09.2007 | CNCF OLQ | Cuba U23 | 6-0 | Cayman Islands U23 | ![]() |
| 11.09.2007 | CNCF OLQ | Cayman Islands U23 | 0-0 | Bermuda U23 | ![]() |
| 09.09.2007 | CNCF OLQ | Puerto Rico U23 | 4-1 | Cayman Islands U23 | ![]() |
CONCACAF
