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 |