Caribbean Championship 2014, Qualifying tournament, Second round, group 8 |
 | 12.10.2014 |  | Haiti | – | Saint Kitts and Nevis |  | 0:0 |
| Port-au-Prince |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 6 |
| 03.09.2014 | | Saint Kitts and Nevis | – | Saint Lucia |  | 0:0 |
| Bassterre |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 08.10.2010 |  | Saint Vincent and Grenadines | – | Saint Kitts and Nevis | | 1:1 (0:1) |
| Kingstown |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 06.10.2010 |  | Barbados | – | Saint Kitts and Nevis | | 1:1 (1:0) |
| Kingstown |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
| 05.11.2008 |  | Guyana | – | Saint Kitts and Nevis | | 1:1 (1:1) |
| Macoya |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
| 20.09.2006 | | Barbados | – | Saint Kitts and Nevis | | 1:1 (1:0) |
| St. John's |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 02.11.2004 | | Saint Kitts and Nevis | – | Saint Lucia | | 1:1 (1:0) |
| Bassterre |
Caribbean Cup 2001, Final tournament, Group 2 |
| 18.05.2001 |  | Cuba | – | Saint Kitts and Nevis | | 1:1 (0:1) |
| Tunapuna |
Caribbean Cup 2001, Qualifying tournament, Group 4 |
| 04.03.2001 |  | Antigua and Barbuda | – | Saint Kitts and Nevis | | 2:2 (0:2) |
| St. John's |
Caribbean Cup 1996, Final tournament, Group A |
| 30.05.1996 |  | Suriname | – | Saint Kitts and Nevis | | 1:1 |
| Port of Spain |
Caribbean Cup 1995, Qualifying tournament, Group 5, Round 2 |
| 21.05.1995 | | Antigua and Barbuda | – | Saint Kitts and Nevis | | 2:2 aet
(2:2),
pen. 4:3 |
| St. John's |
Caribbean Cup 1995, Qualifying tournament, Group 5, Round 2 |
| 30.04.1995 | | Saint Kitts and Nevis | – | Antigua and Barbuda | | 1:1 |
| Bassterre |
Caribbean Cup 1993, Final tournament, Semifinal |
| 28.05.1993 |  | Martinique | – | Saint Kitts and Nevis | | 1:1 aet
(1:1),
pen. 4:3 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 25.05.1993 | | Saint Kitts and Nevis | – | Sint Maarten |  | 2:2 |
| Kingston |
Caribbean Cup 1993, Qualifying tournament, Group 5 |
| 06.04.1993 | | Saint Kitts and Nevis | – | Dominican Republic |  | 2:2 |
| Bassterre |
Caribbean Cup 1991, Qualifying tournament, Group 4 |
| 07.03.1991 | | Saint Kitts and Nevis | – | British Virgin Islands |  | 0:0 |
| Bassterre |
Caribbean Cup 1991, Qualifying tournament, Group 4 |
| 05.03.1991 |  | Cayman Islands | – | Saint Kitts and Nevis | | 1:1 |
| Bassterre |
