| CONCACAF Championship U20 | 2024/02/23 20:00 | Haïti U20 v Kaaimaneilanden U20 | L | 4-1 |
| CONCACAF Championship U20 | 2021/11/10 20:00 | Maagdeneilanden U20 v Kaaimaneilanden U20 | W | 2-5 |
| CONCACAF Championship U20 | 2021/11/08 23:00 | Nicaragua U20 v Kaaimaneilanden U20 | L | 2-1 |
| CONCACAF Championship U20 | 2018/11/10 15:30 | Kaaimaneilanden U20 v Curaçao U20 | L | 2-4 |
| CONCACAF Championship U20 | 2018/11/08 22:30 | Guatemala U20 v Kaaimaneilanden U20 | D | 2-2 |
| CONCACAF Championship U20 | 2018/11/06 15:30 | Guyana U20 v Kaaimaneilanden U20 | W | 2-3 |
| CONCACAF Championship U20 | 2018/11/04 22:30 | Kaaimaneilanden U20 v El Salvador U20 | L | 1-3 |
| CONCACAF Championship U20 | 2024/02/23 23:00 | Puerto Rico U20 v St. Kitts en Nevis U20 | W | 5-0 |
| CONCACAF Championship U20 | 2022/06/27 02:30 | Mexico U20 v Puerto Rico U20 | L | 6-0 |
| CONCACAF Championship U20 | 2021/11/10 23:00 | Puerto Rico U20 v Bermuda U20 | W | 6-0 |
| CONCACAF Championship U20 | 2018/11/09 20:00 | Puerto Rico U20 v St Vincent Grenadines U20 | W | 4-2 |
| CONCACAF Championship U20 | 2018/11/07 20:00 | Puerto Rico U20 v Maagdeneilanden U20 | W | 8-0 |
| CONCACAF Championship U20 | 2018/11/05 20:00 | Suriname U20 v Puerto Rico U20 | W | 1-2 |
| CONCACAF Championship U20 | 2018/11/03 19:00 | Puerto Rico U20 v Trinidad en Tobago U20 | L | 1-5 |
| CONCACAF Championship U20 | 2018/11/01 21:00 | VS U20 v Puerto Rico U20 | L | 7-1 |