Caribbean Championship 2017, Qualifying tournament, Second round, group 5 |
 | 07.06.2016 |  | Saint Vincent and Grenadines | – | Saint Kitts and Nevis |  | 0:1 (0:1) |
| Kingstown |
Caribbean Championship 2017, Qualifying tournament, Second round, group 5 |
| 01.06.2016 | | Saint Kitts and Nevis | – | Suriname |  | 1:0 (1:0) |
| Bassterre |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 1 |
| 29.03.2016 | | Saint Kitts and Nevis | – | Antigua and Barbuda |  | 1:0 (0:0) |
| Bassterre |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 1 |
| 26.03.2016 |  | Aruba | – | Saint Kitts and Nevis | | 0:2 (0:2) |
| Oranjestad |
Caribbean Championship 2014, Qualifying tournament, Second round, group 8 |
| 10.10.2014 |  | French Guiana | – | Saint Kitts and Nevis | | 1:2 (0:1) |
| Port-au-Prince |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 6 |
| 07.09.2014 | | Saint Kitts and Nevis | – | Guyana |  | 2:0 (0:0) |
| Bassterre |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 6 |
| 05.09.2014 | | Saint Kitts and Nevis | – | Dominica |  | 5:0 (3:0) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
| 10.10.2012 | | Saint Kitts and Nevis | – | Anguilla |  | 2:0 (2:0) |
| Bassterre |
Caribbean Championship 2010, Qualifying tournament, Second round, group E |
| 26.10.2010 |  | Puerto Rico | – | Saint Kitts and Nevis | | 0:1 (0:0) |
| Saint George's |
Caribbean Championship 2010, Qualifying tournament, First Round, Group B |
| 10.10.2010 | | Saint Kitts and Nevis | – | Montserrat |  | 4:0 (3:0) |
| Kingstown |
Caribbean Championship 2008, Qualifying tournament, First Round, Group D |
| 24.09.2008 | | Saint Kitts and Nevis | – | British Virgin Islands |  | 4:0 (2:0) |
| Bassterre |
Caribbean Cup 2007, Qualifying tournament, First Round, Group B |
| 22.09.2006 | | Anguilla | – | Saint Kitts and Nevis | | 1:6 (1:2) |
| St. John's |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 04.11.2004 | | Saint Kitts and Nevis | – | Antigua and Barbuda | | 2:0 (2:0) |
| Bassterre |
Caribbean Cup 2005, Qualifying tournament, Group F |
| 31.10.2004 | | Saint Kitts and Nevis | – | Montserrat | | 6:1 (3:0) |
| Bassterre |
Caribbean Cup 2001, Final tournament, Group 2 |
| 20.05.2001 | | Saint Kitts and Nevis | – | Suriname | | 4:0 (1:0) |
| Malabar |
Caribbean Cup 2001, Qualifying tournament, Group 4 |
| 01.03.2001 | | Saint Kitts and Nevis | – | Dominican Republic |  | 2:1 (1:0) |
| St. John's |
Caribbean Cup 1999, Qualifying tournament, Group 3 |
| 20.04.1999 | | Saint Kitts and Nevis | – | Saint Lucia |  | 4:3 |
| Kingstown |
Caribbean Cup 1999, Qualifying tournament, Group 3 |
| 17.04.1999 | | Saint Vincent and Grenadines | – | Saint Kitts and Nevis | | 3:4 (0:3) |
| Kingstown |
Caribbean Cup 1998, Qualifying tournament, Group 3 |
| 05.04.1998 | | Saint Kitts and Nevis | – | Guadeloupe |  | 2:1 |
| |
Caribbean Cup 1998, Qualifying tournament, Group 3 |
| 01.04.1998 | | Saint Kitts and Nevis | – | British Virgin Islands | | 4:0 |
| |
Caribbean Cup 1997, Final tournament, Semifinal |
| 10.07.1997 | | Saint Kitts and Nevis | – | Grenada |  | 2:1 aet
(0:1, 1:1) |
| Bassterre |
Caribbean Cup 1997, Final tournament, Group B |
| 06.07.1997 | | Saint Kitts and Nevis | – | Martinique |  | 2:0 (1:0) |
| Bassterre |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 31.03.1996 | | Saint Kitts and Nevis | – | Sint Maarten |  | 3:0 |
| Bassterre |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 27.03.1996 | | Saint Kitts and Nevis | – | Anguilla | | 8:0 |
| Bassterre |
Caribbean Cup 1995, Qualifying tournament, Group 5, Round 1 |
| 19.03.1995 | | Sint Maarten | – | Saint Kitts and Nevis | | 0:2 |
| Philipsburg |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
| 23.02.1994 | | Saint Kitts and Nevis | – | Montserrat | | 9:1 |
| Bassterre |
Caribbean Cup 1993, Final tournament, Group A |
| 23.05.1993 | | Saint Kitts and Nevis | – | Puerto Rico | | 1:0 |
| Kingston |
Caribbean Cup 1993, Qualifying tournament, Group 5 |
| 02.04.1993 | | Saint Kitts and Nevis | – | British Virgin Islands | | 5:1 |
| Bassterre |
Caribbean Cup 1992, Qualifying tournament, Group 4 |
| 17.04.1992 | | Saint Kitts and Nevis | – | Montserrat | | 10:0 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 4 |
| 15.04.1992 | | Saint Kitts and Nevis | – | British Virgin Islands | | 4:0 |
| |
