Caribbean Championship 2017, Qualifying tournament, First Round, Group 2 |
 | 26.03.2016 |  | Sint Maarten | – | US Virgin Islands |  | 1:2 (0:1) |
| Philipsburg |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 2 |
| 22.03.2016 |  | Grenada | – | Sint Maarten | | 5:0 (0:0) |
| Saint George's |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 31.08.2008 |  | Antigua and Barbuda | – | Sint Maarten | | 3:2 (1:0) |
| George Town |
Caribbean Championship 2008, Qualifying tournament, First Round, Group C |
| 30.08.2008 | | Sint Maarten | – | Bermuda |  | 0:7 (0:3) |
| 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 2001, Qualifying tournament, Group 1 |
| 08.04.2001 | | Sint Maarten | – | Dominica |  | 3:2 (3:1) |
| Georgetown |
Caribbean Cup 2001, Qualifying tournament, Group 1 |
| 06.04.2001 |  | Cuba | – | Sint Maarten | | 1:0 (1:0) |
| Uitvlugt |
Caribbean Cup 2001, Qualifying tournament, Group 1 |
| 04.04.2001 |  | Guyana | – | Sint Maarten | | 2:0 (2:0) |
| Georgetown |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 1 |
| 10.02.2001 | | Sint Maarten | – | Anguilla |  | 3:1 (2:0) |
| Marigot |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 1 |
| 06.02.2001 | | Sint Maarten | – | Montserrat |  | 3:1 (0:0) |
| Philipsburg |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group E |
| 07.03.1999 | | Sint Maarten | – | Aruba |  | -:- |
| |
Caribbean Cup 1999, Qualifying tournament, Preliminary round, group E |
| 20.02.1999 | | Aruba | – | Sint Maarten | | -:- |
| |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 06.04.1997 | | Sint Maarten | – | British Virgin Islands |  | 3:2 |
| Roseau |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 04.04.1997 | | Dominica | – | Sint Maarten | | 1:0 |
| Roseau |
Caribbean Cup 1997, Qualifying tournament, Group 4 |
| 02.04.1997 | | Sint Maarten | – | Anguilla | | 3:0 |
| Roseau |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 31.03.1996 |  | Saint Kitts and Nevis | – | Sint Maarten | | 3:0 |
| Bassterre |
Caribbean Cup 1996, Qualifying tournament, Group 2 |
| 29.03.1996 | | Sint Maarten | – | Anguilla | | 4:0 |
| Bassterre |
Caribbean Cup 1995, Qualifying tournament, Group 5, Round 1 |
| 26.03.1995 | | Saint Kitts and Nevis | – | Sint Maarten | | 0:1 |
| Bassterre |
Caribbean Cup 1995, Qualifying tournament, Group 5, Round 1 |
| 19.03.1995 | | Sint Maarten | – | Saint Kitts and Nevis | | 0:2 |
| Philipsburg |
Caribbean Cup 1994, Qualifying tournament, Group 5 |
| 06.03.1994 | | Sint Maarten | – | British Virgin Islands | | 3:0 |
| 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 |  | Jamaica | – | Sint Maarten | | 4:2 aet
(2:2) |
| George Town |
Caribbean Cup 1993, Final tournament, Group A |
| 25.05.1993 | | Saint Kitts and Nevis | – | Sint Maarten | | 2:2 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 23.05.1993 | | Jamaica | – | Sint Maarten | | 2:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
| 21.05.1993 |  | Puerto Rico | – | Sint Maarten | | 3:0 |
| Kingston |
Caribbean Cup 1993, Qualifying tournament, Group 4 |
| 06.04.1993 | | Anguilla | – | Sint Maarten | | 0:1 |
| The Valley |
Caribbean Cup 1993, Qualifying tournament, Group 4 |
| 05.04.1993 | | Antigua and Barbuda | – | Sint Maarten | | 0:1 |
| The Valley |
Caribbean Cup 1992, Qualifying tournament, Group 2 |
| 05.04.1992 | | Sint Maarten | – | Martinique |  | 1:1 |
| |
Caribbean Cup 1992, Qualifying tournament, Group 2 |
| 03.04.1992 | | Sint Maarten | – | Cayman Islands | | 4:2 |
| |
Caribbean Cup 2005, Qualifying tournament, Group A, Preliminary Round |
| |  | St. Martin | – | Sint Maarten | | +:- |
| |
