| Date | Competition | Outcome | Home team | Score/Time | Visiting Team | ||
|---|---|---|---|---|---|---|---|
| 07/29/1995 | Caribbe… | L |
Cayman Islands | 0 - 3 | Cuba | More info | |
| 10/21/1995 | Friendlies | L |
Cayman Islands | 1 - 5 | Jamaica | More info | |
| 10/23/1995 | Friendlies | L |
Cayman Islands | 0 - 7 | Trinidad an… | More info | |
| 05/11/1996 | WC Qual… | L |
Cayman Islands | 0 - 1 | Cuba | More info | |
| 05/13/1996 | WC Qual… | L |
Cuba | 5 - 0 | Cayman Islands | More info | |
| 07/21/1998 | Caribbe… | L |
Cayman Islands | 0 - 4 | Jamaica | More info | |
| 07/23/1998 | Caribbe… | W |
Cayman Islands | 2 - 0 | Curaçao | More info | |
| 07/25/1998 | Caribbe… | L |
Haiti | 1 - 0 | Cayman Islands | More info | |
| 09/08/1999 | Friendlies | L |
Bermuda | 3 - 1 | Cayman Islands | More info | |
| 09/10/1999 | Friendlies | L |
Bermuda | 1 - 0 | Cayman Islands | More info | |
| 09/22/1999 | Friendlies | W |
Cayman Islands | 4 - 0 | Bahamas | More info | |
| 10/23/1999 | Friendlies | L |
Jamaica | 4 - 1 | Cayman Islands | More info | |
| 02/05/2000 | Friendlies | D |
Cayman Islands | 0 - 0 | Jamaica | More info | |
| 02/08/2000 | Friendlies | L |
Cayman Islands | 0 - 1 | Jamaica | More info | |
| 03/04/2000 | WC Qual… | L |
Cuba | 4 - 0 | Cayman Islands | More info | |
| 03/18/2000 | WC Qual… | D |
Cayman Islands | 0 - 0 | Cuba | More info | |
| 08/26/2000 | Friendlies | L |
Cayman Islands | 0 - 6 | Jamaica | More info | |
| 09/26/2000 | Friendlies | W |
Cayman Islands | 3 - 0 | Turks and C… | More info | |
| 02/24/2001 | Friendlies | L |
Cayman Islands | 0 - 3 | Trinidad an… | More info | |
| 11/16/2002 | Friendlies | L |
Cayman Islands | 0 - 1 | Nicaragua | More info | |
| 11/26/2002 | Caribbe… | L |
Cayman Islands | 0 - 5 | Cuba | More info | |
| 11/28/2002 | Caribbe… | W |
Cayman Islands | 1 - 0 | Dominican R… | More info | |
| 11/30/2002 | Caribbe… | L |
Cayman Islands | 0 - 3 | Martinique | More info | |
| 02/21/2004 | WC Qual… | L |
Cayman Islands | 1 - 2 | Cuba | More info | |
| 03/26/2004 | WC Qual… | L |
Cuba | 3 - 0 | Cayman Islands | More info | |
| 11/23/2004 | Caribbe… | L |
Cayman Islands | 1 - 2 | Bermuda | More info | |
| 11/25/2004 | Caribbe… | W |
British Vir… | 0 - 1 | Cayman Islands | More info | |
| 11/27/2004 | Caribbe… | L |
St. Vincen… | 4 - 0 | Cayman Islands | More info | |
| 09/01/2006 | Caribbe… | L |
Bahamas | 3 - 1 | Cayman Islands | More info | |
| 09/03/2006 | Caribbe… | L |
Cayman Islands | 0 - 2 | Turks and C… | More info | |
| 09/05/2006 | Caribbe… | L |
Cuba | 7 - 0 | Cayman Islands | More info | |
| 02/03/2008 | WC Qual… | D |
Bermuda | 1 - 1 | Cayman Islands | View events | More info |
| 03/30/2008 | WC Qual… | L |
Cayman Islands | 1 - 3 | Bermuda | View events | More info |
| 08/26/2008 | Caribbe… | W |
Cayman Islands | 3 - 0 | Saint Martin | More info | |
| 08/29/2008 | Caribbe… | D |
Cayman Islands | 1 - 1 | Antigua an… | More info | |
| 08/30/2008 | Caribbe… | D |
Cayman Islands | 0 - 0 | Bermuda | More info | |
| 10/10/2008 | Caribbe… | L |
Guadeloupe | 7 - 1 | Cayman Islands | More info | |
| 10/12/2008 | Caribbe… | L |
Cayman Islands | 0 - 1 | Martinique | More info | |
| 10/14/2008 | Caribbe… | L |
Grenada | 4 - 2 | Cayman Islands | More info | |
| 11/08/2008 | Friendlies | L |
Cayman Islands | 0 - 2 | Jamaica | More info | |
| 06/28/2009 | Friendlies | L |
Cayman Islands | 1 - 4 | Jamaica | View events | More info |
| 10/02/2010 | Caribbe… | D |
Saint Martin | 1 - 1 | Cayman Islands | View events | More info |
| 10/04/2010 | Caribbe… | W |
Cayman Islands | 4 - 1 | Anguilla | View events | More info |
| 10/06/2010 | Caribbe… | L |
Puerto Rico | 2 - 0 | Cayman Islands | View events | More info |
| 09/02/2011 | WC Qual… | L |
Suriname | 1 - 0 | Cayman Islands | View events | More info |
| 09/06/2011 | WC Qual… | L |
Cayman Islands | 1 - 4 | El Salvador | View events | More info |
| 10/07/2011 | WC Qual… | L |
Cayman Islands | 0 - 1 | Suriname | View events | More info |
| 10/11/2011 | WC Qual… | L |
El Salvador | 4 - 0 | Cayman Islands | View events | More info |
| 11/11/2011 | WC Qual… | L |
Dominican R… | 4 - 0 | Cayman Islands | View events | More info |
| 11/14/2011 | WC Qual… | D |
Cayman Islands | 1 - 1 | Dominican R… | View events | More info |