Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
 | 06.10.2010 |  | Puerto Rico | – | Cayman Islands |  | 2:0 (1:0) |
| Bayamón |
Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
| 04.10.2010 | | Cayman Islands | – | Anguilla |  | 4:1 (1:1) |
| Bayamón |
Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
| 02.10.2010 |  | St. Martin | – | Cayman Islands | | 1:1 (0:1) |
| Bayamón |
Caribbean Championship 2008, Qualifying tournament, Second round, group F |
| 15.10.2008 |  | Grenada | – | Cayman Islands | | 4:2 (2:1) |
| Les Abymes |
Caribbean Championship 2008, Qualifying tournament, Second round, group F |
| 13.10.2008 | | Cayman Islands | – | Martinique |  | 0:1 (0:1) |
| Les Abymes |
Caribbean Championship 2008, Qualifying tournament, Second round, group F |
| 11.10.2008 |  | Guadeloupe | – | Cayman Islands | | 7:1 (3:0) |
| Les Abymes |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 31.08.2008 | | Cayman Islands | – | Bermuda |  | 0:0 |
| George Town |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 30.08.2008 | | Cayman Islands | – | Antigua and Barbuda |  | 1:1 (0:1) |
| George Town |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 27.08.2008 | | Cayman Islands | – | Sint Maarten |  | 3:0 (0:0) |
| George Town |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 06.09.2006 |  | Cuba | – | Cayman Islands | | 7:0 (4:0) |
| La Habana |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 04.09.2006 | | Cayman Islands | – | Turks and Caicos Islands |  | 0:2 (0:1) |
| La Habana |
Caribbean Cup 2007, Qualifying tournament, First Round, Group E |
| 02.09.2006 |  | Bahamas | – | Cayman Islands | | 3:1 (2:0) |
| La Habana |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 28.11.2004 |  | Saint Vincent and Grenadines | – | Cayman Islands | | 4:0 (2:0) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 26.11.2004 | | Cayman Islands | – | British Virgin Islands |  | 1:0 (0:0) |
| Kingstown |
Caribbean Cup 2005, Qualifying tournament, Group E |
| 24.11.2004 | | Bermuda | – | Cayman Islands | | 2:1 (2:0) |
| Kingstown |
Caribbean Cup 2001, Qualifying tournament, Group 2 |
| 08.04.2001 | | Martinique | – | Cayman Islands | | 1:1 (1:1) |
| Fort-de-France |
Caribbean Cup 2001, Qualifying tournament, Group 2 |
| 06.04.2001 | | Saint Vincent and Grenadines | – | Cayman Islands | | 1:1 (1:1) |
| Lamentin |
Caribbean Cup 2001, Qualifying tournament, Group 2 |
| 04.04.2001 | | Cayman Islands | – | British Virgin Islands | | 2:2 (1:1) |
| Fort-de-France |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 09.05.1999 | | Cayman Islands | – | Bahamas | | 4:1 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 07.05.1999 | | Bermuda | – | Cayman Islands | | 4:1 |
| Hamilton |
Caribbean Cup 1999, Qualifying tournament, Group 1 |
| 05.05.1999 | | Cayman Islands | – | Cuba | | 1:4 (1:3) |
| Hamilton |
Caribbean Cup 1998, Final tournament, Group B |
| 26.07.1998 |  | Netherlands Antilles | – | Cayman Islands | | 0:2 |
| |
Caribbean Cup 1998, Final tournament, Group B |
| 24.07.1998 | | Cayman Islands | – | Haiti |  | 0:1 |
| |
Caribbean Cup 1998, Final tournament, Group B |
| 22.07.1998 |  | Jamaica | – | Cayman Islands | | 4:0 |
| |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 10.05.1998 | | Cayman Islands | – | Bermuda | | 2:0 |
| |
Caribbean Cup 1998, Qualifying tournament, Group 6 |
| 06.05.1998 | | Cayman Islands | – | Cuba | | 2:2 |
| |
Caribbean Cup 1996, Qualifying tournament, Group 4 |
| 26.04.1996 | | Cuba | – | Cayman Islands | | 4:0 |
| |
Caribbean Cup 1995, Final tournament, 3rd place match |
| 30.07.1995 | | Cayman Islands | – | Cuba | | 0:3 (0:1) |
| Cayman Islands |
Caribbean Cup 1995, Final tournament, Semifinal |
| 28.07.1995 | | Cayman Islands | – | Trinidad and Tobago |  | 2:9 (1:2) |
| Cayman Islands |
Caribbean Cup 1995, Final tournament, Group A |
| 25.07.1995 | | Cayman Islands | – | Saint Vincent and Grenadines | | 2:2 (2:1) |
| |
Caribbean Cup 1995, Final tournament, Group A |
| 23.07.1995 | | Cayman Islands | – | French Guiana |  | 1:0 (0:0) |
| |
Caribbean Cup 1995, Final tournament, Group A |
| 21.07.1995 | | Cayman Islands | – | Antigua and Barbuda | | 2:0 (1:0) |
| |
Caribbean Cup 1994, Final tournament, Group B |
| 11.04.1994 | | Martinique | – | Cayman Islands | | 1:1 |
| San Fernando |
Caribbean Cup 1994, Final tournament, Group B |
| 09.04.1994 |  | Suriname | – | Cayman Islands | | 2:0 |
| San Fernando |
Caribbean Cup 1994, Final tournament, Group B |
| 07.04.1994 | | Haiti | – | Cayman Islands | | 3:2 |
| San Fernando |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 06.03.1994 | | Cayman Islands | – | Jamaica | | 3:2 (2:1) |
| George Town |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 04.03.1994 | | Cayman Islands | – | Sint Maarten | | 5:0 |
| George Town |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 02.03.1994 | | Cayman Islands | – | British Virgin Islands | | 5:0 |
| George Town |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
| 14.03.1993 | | Puerto Rico | – | Cayman Islands | | 4:0 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
| 12.03.1993 | | Cayman Islands | – | Barbados |  | 1:6 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
| 11.03.1993 |  | Guyana | – | Cayman Islands | | 3:2 |
| Georgetown |
Caribbean Cup 1992, Qualifying tournament, Group 2 |
| 03.04.1992 | | Sint Maarten | – | Cayman Islands | | 4:2 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 2 |
| 01.04.1992 | | Martinique | – | Cayman Islands | | 7:0 |
| |
Caribbean Cup 1991, Final tournament, Group A |
| 27.05.1991 | | Jamaica | – | Cayman Islands | | 3:2 |
| Kingston |
Caribbean Cup 1991, Final tournament, Group A |
| 25.05.1991 | | Guyana | – | Cayman Islands | | 2:1 |
| Kingston |
Caribbean Cup 1991, Qualifying tournament, Group 4 |
| 09.03.1991 | | Cayman Islands | – | British Virgin Islands | | 2:1 |
| Bassterre |
Caribbean Cup 1991, Qualifying tournament, Group 4 |
| 05.03.1991 | | Cayman Islands | – | Saint Kitts and Nevis |  | 1:1 |
| Bassterre |
Superclásico
Copa Newton
Copa Lipton
Copa Rosa
Copa Félix Bogado
Copa Carlos Dittborn
Copa Ramón Castilla
Copa Rio Branco
Copa Rodrigues Alves
Taça Bernardo O'Higgins
Copa Artigas
Copa Paz del Chaco
Copa del Pacífico
