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 |
| |
