Caribbean Championship 2017, Qualifying tournament, Third round, group 2 |
 | 13.11.2016 |  | Saint Kitts and Nevis | | Haiti |  | 0:2 aet (0:0) |
| Bassterre |
Caribbean Championship 2017, Qualifying tournament, Third round, group 2 |
 | 08.10.2016 |  | French Guiana | | Saint Kitts and Nevis |  | 1:0 (0:0) |
| Remire-Montjoly |
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 |
 | 12.10.2014 |  | Haiti | | Saint Kitts and Nevis |  | 0:0 |
| Port-au-Prince |
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, Second round, group 8 |
 | 08.10.2014 |  | Saint Kitts and Nevis | | Barbados |  | 2:3 (1:3) |
| 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 2014, Qualifying tournament, First Round, Group 6 |
 | 03.09.2014 |  | Saint Kitts and Nevis | | Saint Lucia |  | 0:0 |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
 | 14.10.2012 |  | Saint Kitts and Nevis | | French Guiana |  | 0:3 (0:2) |
| Bassterre |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 5 |
 | 12.10.2012 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:1 (0:0) |
| 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, Second round, group E |
 | 24.10.2010 |  | Grenada | | Saint Kitts and Nevis |  | 2:0 (2:0) |
| Saint George's |
Caribbean Championship 2010, Qualifying tournament, Second round, group E |
 | 22.10.2010 |  | Saint Kitts and Nevis | | Guadeloupe |  | 1:2 (0:1) |
| 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 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 |
 | 09.11.2008 |  | Saint Kitts and Nevis | | Antigua and Barbuda |  | 3:4 (0:2) |
| Macoya |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
 | 07.11.2008 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 3:1 (1:0) |
| Macoya |
Caribbean Championship 2008, Qualifying tournament, Second round, group H |
 | 05.11.2008 |  | Guyana | | Saint Kitts and Nevis |  | 1:1 (1:1) |
| Macoya |
Caribbean Championship 2008, Qualifying tournament, First Round, Group D |
 | 28.09.2008 |  | Saint Kitts and Nevis | | Barbados |  | 1:3 (1:2) |
| Bassterre |
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 |
 | 24.09.2006 |  | Antigua and Barbuda | | Saint Kitts and Nevis |  | 1:0 (0:0) |
| St. John's |
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 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, Second round |
 | 15.12.2004 |  | Saint Kitts and Nevis | | Haiti |  | 0:2 (0:1) |
| Bassterre |
Caribbean Cup 2005, Qualifying tournament, Second round |
 | 12.12.2004 |  | Haiti | | Saint Kitts and Nevis |  | 1:0 (0:0) |
| USA, Fort Lauderdale |
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 |
 | 02.11.2004 |  | Saint Kitts and Nevis | | Saint Lucia |  | 1:1 (1:0) |
| 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, Final tournament, Group 2 |
 | 18.05.2001 |  | Cuba | | Saint Kitts and Nevis |  | 1:1 (0:1) |
| Tunapuna |
Caribbean Cup 2001, Final tournament, Group 2 |
 | 16.05.2001 |  | Haiti | | Saint Kitts and Nevis |  | 7:2 (3:1) |
| 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 2001, Qualifying tournament, Group 4 |
 | 01.03.2001 |  | Saint Kitts and Nevis | | Dominican Republic |  | 2:1 (1:0) |
| St. John's |
Caribbean Cup 1999, Final tournament, Group B |
 | 08.06.1999 |  | Cuba | | Saint Kitts and Nevis |  | 2:0 (1:0) |
| Macoya |
Caribbean Cup 1999, Final tournament, Group B |
 | 06.06.1999 |  | Saint Kitts and Nevis | | Haiti |  | 0:2 (0:1) |
| Macoya |
Caribbean Cup 1999, Final tournament, Group B |
 | 04.06.1999 |  | Saint Kitts and Nevis | | Brazil U20 |  | 0:5 (0:1) |
| Macoya |
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 |
 | 18.04.1999 |  | Saint Kitts and Nevis | | Martinique |  | 1:2 (0:2) |
| 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 |
 | 03.04.1998 |  | Saint Kitts and Nevis | | Dominica |  | 1:2 |
| |
Caribbean Cup 1998, Qualifying tournament, Group 3 |
 | 01.04.1998 |  | Saint Kitts and Nevis | | British Virgin Islands |  | 4:0 |
| |
Caribbean Cup 1997, Final tournament, Final |
 | 13.07.1997 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:4 (0:2) |
| Bassterre |
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 |
 | 08.07.1997 |  | Saint Kitts and Nevis | | Trinidad and Tobago |  | 0:3 (0:3) |
| Bassterre |
Caribbean Cup 1997, Final tournament, Group B |
 | 06.07.1997 |  | Saint Kitts and Nevis | | Martinique |  | 2:0 (1:0) |
| Bassterre |
Caribbean Cup 1996, Final tournament, Group A |
 | 30.05.1996 |  | Suriname | | Saint Kitts and Nevis |  | 1:1 |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
 | 28.05.1996 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 5:1 |
| Port of Spain |
Caribbean Cup 1996, Final tournament, Group A |
 | 26.05.1996 |  | Jamaica | | Saint Kitts and Nevis |  | 4:1 (1:0) |
| Palo Seco |
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 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 1995, Qualifying tournament, Group 5, Round 1 |
 | 26.03.1995 |  | Saint Kitts and Nevis | | Sint Maarten |  | 0:1 |
| 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 |
 | 27.02.1994 |  | Saint Kitts and Nevis | | Antigua and Barbuda |  | -:- |
| |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
 | 25.02.1994 |  | Saint Kitts and Nevis | | Dominica |  | 2:4 aet (2:2) |
| Bassterre |
Caribbean Cup 1994, Qualifying tournament, Group 4 |
 | 23.02.1994 |  | Saint Kitts and Nevis | | Montserrat |  | 9:1 |
| Bassterre |
Caribbean Cup 1993, Final tournament, 3rd place match |
 | 30.05.1993 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 3:2 |
| Kingston |
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, Final tournament, Group A |
 | 23.05.1993 |  | Saint Kitts and Nevis | | Puerto Rico |  | 1:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
 | 21.05.1993 |  | Jamaica | | Saint Kitts and Nevis |  | 4:1 |
| Kingston |
Caribbean Cup 1993, Qualifying tournament, Group 5 |
 | 06.04.1993 |  | Saint Kitts and Nevis | | Dominican Republic |  | 2:2 |
| Bassterre |
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 |
 | 19.04.1992 |  | Saint Kitts and Nevis | | Antigua and Barbuda |  | 0:1 |
| |
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 |
| |
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 |
Caribbean Cup 1989, Qualifying tournament, Zone A |
 | ??.06.1989 |  | Trinidad and Tobago | | Saint Kitts and Nevis |  | 2:0 |
| |