| Date | Competition | Outcome | Home team | Score/Time | Visiting Team | ||
|---|---|---|---|---|---|---|---|
| 07/03/1999 | Olympi… | D |
Dominica U23 | 1 - 1 | St Kitts an… | More info | |
| 07/17/1999 | Olympi… | W |
St Kitts an… | 2 - 0 | Dominica U23 | More info | |
| 09/18/1999 | Olympi… | L |
St Kitts an… | 1 - 3 | Jamaica U23 | More info | |
| 09/25/1999 | Olympi… | L |
Jamaica U23 | 2 - 1 | St Kitts an… | More info | |
| 09/06/2003 | Olympi… | W |
Dominica U23 | 0 - 1 | St Kitts an… | More info | |
| 10/10/2003 | Olympi… | W |
St Kitts an… | 3 - 1 | Dominica U23 | More info | |
| 11/14/2003 | Olympi… | L |
St Kitts an… | 0 - 6 | United Stat… | More info | |
| 11/18/2003 | Olympi… | L |
United Stat… | 4 - 0 | St Kitts an… | More info | |
| 09/08/2007 | Olympi… | D |
St Kitts an… | 1 - 1 | Dominican R… | More info | |
| 09/12/2007 | Olympi… | L |
St Kitts an… | 0 - 1 | Haiti U23 | More info | |
| 07/21/2011 | Olympi… | W |
St Kitts an… | 2 - 1 | St. Lucia U23 | View events | More info |
| 07/23/2011 | Olympi… | W |
St Kitts an… | 2 - 1 | Antigua an… | View events | More info |
| 07/25/2011 | Olympi… | W |
St Kitts an… | 2 - 1 | Haiti U23 | View events | More info |
| 11/24/2011 | Olympi… | L |
St Kitts an… | 0 - 1 | Suriname U23 | View events | More info |
| 11/26/2011 | Olympi… | W |
St Kitts an… | 5 - 2 | Trinidad an… | View events | More info |
| 11/28/2011 | Olympi… | D |
St Kitts an… | 1 - 1 | Cuba U23 | View events | More info |