World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group A |
 | 07.06.2025 |  | Cayman Islands | – | Honduras |  | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group A |
| 04.06.2025 |  | Bermuda | – | Cayman Islands | | |
| |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group A |
| 11.06.2024 |  | Cuba | – | Cayman Islands | | * |
| Santiago de Cuba |
World Cup 2026, Qualifying tournament, CONCACAF, Second Round, Group A |
| 08.06.2024 | | Cayman Islands | – | Antigua and Barbuda |  | 1:0 (0:0) |
| George Town |
World Cup 2022, Qualifying tournament, CONCACAF, Group B |
| 08.06.2021 | | Bermuda | – | Cayman Islands | | 1:1 (0:1) |
| USA, Bradenton IMG Academy |
World Cup 2022, Qualifying tournament, CONCACAF, Group B |
| 02.06.2021 | | Cayman Islands | – | Aruba |  | 1:3 (1:2) |
| USA, Bradenton IMG Academy |
World Cup 2022, Qualifying tournament, CONCACAF, Group B |
| 29.03.2021 | | Cayman Islands | – | Canada |  | 0:11 (0:6) |
| USA, Bradenton IMG Academy |
World Cup 2022, Qualifying tournament, CONCACAF, Group B |
| 24.03.2021 |  | Suriname | – | Cayman Islands | | 3:0 (2:0) * |
| Paramaribo |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 29.03.2015 | | Cayman Islands | – | Belize |  | 1:1 (1:1) |
| George Town |
World Cup 2018, Qualifying tournament, CONCACAF, First Round |
| 25.03.2015 | | Belize | – | Cayman Islands | | 0:0 |
| Belmopan |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 14.11.2011 | | Cayman Islands | – | Dominican Republic |  | 1:1 (0:1) |
| George Town |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 11.11.2011 | | Dominican Republic | – | Cayman Islands | | 4:0 (2:0) |
| San Cristóbal |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 11.10.2011 |  | El Salvador | – | Cayman Islands | | 4:0 (4:0) |
| San Salvador |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 07.10.2011 | | Cayman Islands | – | Suriname | | 0:1 (0:0) |
| George Town |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 06.09.2011 | | Cayman Islands | – | El Salvador | | 1:4 (0:0) |
| George Town |
World Cup 2014, Qualifying tournament, CONCACAF, Second round, group A |
| 02.09.2011 | | Suriname | – | Cayman Islands | | 1:0 (1:0) |
| Paramaribo |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 30.03.2008 | | Cayman Islands | – | Bermuda | | 1:3 (0:2) |
| George Town |
World Cup 2010, Qualifying tournament, CONCACAF, First Round |
| 03.02.2008 | | Bermuda | – | Cayman Islands | | 1:1 (1:0) |
| Hamilton |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 27.03.2004 | | Cuba | – | Cayman Islands | | 3:0 (1:0) |
| La Habana |
World Cup 2006, Qualifying tournament, CONCACAF, First Round |
| 22.02.2004 | | Cayman Islands | – | Cuba | | 1:2 (0:0) |
| George Town |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 1 |
| 19.03.2000 | | Cayman Islands | – | Cuba | | 0:0 aet,
pen. 4:0 |
| George Town |
World Cup 2002, Qualifying tournament, CONCACAF, Caribbean Zone, Round 1, Group 1 |
| 05.03.2000 | | Cuba | – | Cayman Islands | | 4:0 (1:0) |
| La Habana |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Second Round |
| 14.05.1996 | | Cayman Islands | – | Cuba | | 0:5 (0:1) |
| George Town |
World Cup 1998, Qualifying tournament, CONCACAF, Caribbean Zone, Second Round |
| 12.05.1996 | | Cayman Islands | – | Cuba | | 0:1 (0:1) |
| George Town |
