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 |
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