World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
 | 10.06.2025 | | Saint Kitts and Nevis | – | Grenada | | 2:3 (1:0) |
| Bassterre |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 06.06.2025 | | Trinidad and Tobago | – | Saint Kitts and Nevis | | 6:2 (2:2) |
| Port of Spain |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group B |
| 06.06.2024 | | Costa Rica | – | Saint Kitts and Nevis | | 4:0 (1:0) |
| San José |
World Cup 2022, Qualifying tournament, CONCACAF, Second round |
| 15.06.2021 | | El Salvador | – | Saint Kitts and Nevis | | 2:0 (1:0) |
| San Salvador |
World Cup 2022, Qualifying tournament, CONCACAF, Second round |
| 12.06.2021 | | Saint Kitts and Nevis | – | El Salvador | | 0:4 (0:3) |
| Bassterre |
World Cup 2022, Qualifying tournament, CONCACAF, Group F |
| 08.06.2021 | | Trinidad and Tobago | – | Saint Kitts and Nevis | | 2:0 (1:0) |
| Dominican Republic, Santo Domingo de Guzmán |
World Cup 2018, Qualifying tournament, CONCACAF, Second round |
| 16.06.2015 | | El Salvador | – | Saint Kitts and Nevis | | 4:1 (1:0) |
| San Salvador |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group D |
| 15.11.2011 | | Canada | – | Saint Kitts and Nevis | | 4:0 (3:0) |
| Toronto |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 06.02.2008 | | Belize | – | Saint Kitts and Nevis | | 3:1 (3:1) |
| Guatemala, Ciudad de Guatemala |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 17.11.2004 | | Mexico | – | Saint Kitts and Nevis | | 8:0 (2:0) |
| Monterrey |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 13.11.2004 | | Saint Kitts and Nevis | – | Mexico | | 0:5 (0:2) |
| USA, Miami |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 13.10.2004 | | Saint Kitts and Nevis | – | Saint Vincent and Grenadines | | 0:3 (0:1) |
| Bassterre |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 10.10.2004 | | Trinidad and Tobago | – | Saint Kitts and Nevis | | 5:1 (2:1) |
| San Fernando |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 10.09.2004 | | Saint Vincent and Grenadines | – | Saint Kitts and Nevis | | 1:0 (1:0) |
| Kingstown |
World Cup 2006, Qualifying tournament, CONCACAF, Third round, group C |
| 04.09.2004 | | Saint Kitts and Nevis | – | Trinidad and Tobago | | 1:2 (1:1) |
| Bassterre |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 2 |
| 22.04.2000 | | Saint Kitts and Nevis | – | Saint Vincent and Grenadines | | 1:2 (0:1) |
| Bassterre |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 2 |
| 16.04.2000 | | Saint Vincent and Grenadines | – | Saint Kitts and Nevis | | 1:0 (0:0) |
| Kingstown |
