| CONCACAF U20 Championship | 2022/06/22 20:00 | Canada U20 v St Kitts & Nevis U20 | L | 4-0 |
| CONCACAF U20 Championship | 2022/06/20 20:00 | St Kitts & Nevis U20 v Cuba U20 | L | 0-6 |
| CONCACAF U20 Championship | 2022/06/18 20:00 | USA U20 v St Kitts & Nevis U20 | L | 10-0 |
| CONCACAF U20 Championship | 2018/11/10 22:30 | Panama U20 v St Kitts & Nevis U20 | L | 2-1 |
| CONCACAF U20 Championship | 2018/11/08 20:00 | Canada U20 v St Kitts & Nevis U20 | W | 1-2 |
| CONCACAF U20 Championship | 2018/11/06 17:45 | St Kitts & Nevis U20 v Guadeloupe U20 | L | 2-3 |
| CONCACAF U20 Championship | 2018/11/04 17:45 | Dominica U20 v St Kitts & Nevis U20 | L | 3-2 |
| CONCACAF U20 Championship | 2018/11/02 16:45 | St Kitts & Nevis U20 v Martinique U20 | L | 0-1 |
| CONCACAF U20 Championship | 2021/11/10 20:00 | US Virgin Islands U20 v Cayman Islands U20 | W | 2-5 |
| CONCACAF U20 Championship | 2021/11/08 23:00 | Nicaragua U20 v Cayman Islands U20 | L | 2-1 |
| CONCACAF U20 Championship | 2018/11/10 15:30 | Cayman Islands U20 v Curacao U20 | L | 2-4 |
| CONCACAF U20 Championship | 2018/11/08 22:30 | Guatemala U20 v Cayman Islands U20 | D | 2-2 |
| CONCACAF U20 Championship | 2018/11/06 15:30 | Guyana U20 v Cayman Islands U20 | W | 2-3 |
| CONCACAF U20 Championship | 2018/11/04 22:30 | Cayman Islands U20 v El Salvador U20 | L | 1-3 |