Caribbean Championship 2017, Qualifying tournament, Third round, group 3 |
 | 11.10.2016 |  | Puerto Rico | | Curaçao |  | 2:4 aet (2:0, 2:2) |
| Bayamón |
Caribbean Championship 2017, Qualifying tournament, Third round, group 3 |
 | 08.10.2016 |  | Antigua and Barbuda | | Puerto Rico |  | 2:0 (1:0) |
| St. John's |
Caribbean Championship 2017, Qualifying tournament, Second round, group 1 |
 | 04.06.2016 |  | Puerto Rico | | Antigua and Barbuda |  | 2:1 aet (1:1, 1:1) |
| Bayamón |
Caribbean Championship 2017, Qualifying tournament, Second round, group 1 |
 | 01.06.2016 |  | Grenada | | Puerto Rico |  | 3:3 aet (3:3, 3:3), pen. 3:4 |
| Saint George's |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 5 |
 | 29.03.2016 |  | Puerto Rico | | Guyana |  | 0:1 (0:0) |
| Bayamón |
Caribbean Championship 2017, Qualifying tournament, First Round, Group 5 |
 | 26.03.2016 |  | Anguilla | | Puerto Rico |  | 0:4 (0:2) |
| The Valley Raymond E. Guishard Technical Centre |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 4 |
 | 07.09.2014 |  | Puerto Rico | | Grenada |  | 2:2 (1:0) |
| Bayamón |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 4 |
 | 05.09.2014 |  | Puerto Rico | | French Guiana |  | 1:2 (1:0) |
| Bayamón |
Caribbean Championship 2014, Qualifying tournament, First Round, Group 4 |
 | 03.09.2014 |  | Puerto Rico | | Curaçao |  | 2:2 (1:0) |
| Bayamón |
Caribbean Championship 2012, Qualifying tournament, Second round, group 7 |
 | 27.10.2012 |  | Puerto Rico | | Dominican Republic |  | 1:3 (0:1) |
| Les Abymes |
Caribbean Championship 2012, Qualifying tournament, Second round, group 7 |
 | 25.10.2012 |  | Guadeloupe | | Puerto Rico |  | 4:1 (3:0) |
| Les Abymes |
Caribbean Championship 2012, Qualifying tournament, Second round, group 7 |
 | 23.10.2012 |  | Martinique | | Puerto Rico |  | 2:1 (2:0) |
| Les Abymes |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
 | 11.09.2012 |  | Haiti | | Puerto Rico |  | 2:1 (0:0) |
| Port-au-Prince |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
 | 09.09.2012 |  | Puerto Rico | | St. Martin |  | 9:0 (4:0) |
| Port-au-Prince |
Caribbean Championship 2012, Qualifying tournament, First Round, Group 1 |
 | 07.09.2012 |  | Bermuda | | Puerto Rico |  | 1:2 (0:0) |
| Port-au-Prince |
Caribbean Championship 2010, Qualifying tournament, Second round, group E |
 | 26.10.2010 |  | Puerto Rico | | Saint Kitts and Nevis |  | 0:1 (0:0) |
| Saint George's |
Caribbean Championship 2010, Qualifying tournament, Second round, group E |
 | 24.10.2010 |  | Guadeloupe | | Puerto Rico |  | 3:2 (2:0) |
| Saint George's |
Caribbean Championship 2010, Qualifying tournament, Second round, group E |
 | 22.10.2010 |  | Grenada | | Puerto Rico |  | 3:1 (1:0) |
| Saint George's |
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 |  | Puerto Rico | | St. Martin |  | 2:0 (1:0) |
| Bayamón |
Caribbean Championship 2010, Qualifying tournament, First Round, Group A |
 | 02.10.2010 |  | Puerto Rico | | Anguilla |  | 3:1 (2:0) |
| Bayamón |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 28.11.2004 |  | Grenada | | Puerto Rico |  | 5:2 (2:0) |
| Malabar |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 26.11.2004 |  | Puerto Rico | | Suriname |  | 1:1 (0:1) |
| San Fernando |
Caribbean Cup 2005, Qualifying tournament, Group D |
 | 24.11.2004 |  | Trinidad and Tobago | | Puerto Rico |  | 5:0 (2:0) |
| Macoya |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 2 |
 | 11.02.2001 |  | British Virgin Islands | | Puerto Rico |  | 0:0 |
| Road Town |
Caribbean Cup 2001, Qualifying tournament, Preliminary round, group 2 |
 | 03.02.2001 |  | Puerto Rico | | British Virgin Islands |  | 1:2 (0:1) |
| San Juan |
Caribbean Cup 1999, Qualifying tournament, Group 4 |
 | 21.03.1999 |  | Dominican Republic | | Puerto Rico |  | 2:0 |
| Port-au-Prince |
Caribbean Cup 1999, Qualifying tournament, Group 4 |
 | 19.03.1999 |  | Puerto Rico | | British Virgin Islands |  | 0:5 |
| Port-au-Prince |
Caribbean Cup 1999, Qualifying tournament, Group 4 |
 | 17.03.1999 |  | Haiti | | Puerto Rico |  | 2:0 |
| Port-au-Prince |
Caribbean Cup 1998, Qualifying tournament, Group 5 |
 | 13.03.1998 |  | Dominican Republic | | Puerto Rico |  | 3:1 |
| Port-au-Prince |
Caribbean Cup 1998, Qualifying tournament, Group 5 |
 | 11.03.1998 |  | Haiti | | Puerto Rico |  | 4:0 |
| Port-au-Prince |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
 | 27.05.1995 |  | Cuba | | Puerto Rico |  | 9:0 |
| La Habana |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
 | 25.05.1995 |  | Puerto Rico | | Netherlands Antilles |  | 2:2 |
| La Habana |
Caribbean Cup 1995, Qualifying tournament, Group 1 |
 | 23.05.1995 |  | Dominican Republic | | Puerto Rico |  | 3:1 |
| La Habana |
Caribbean Cup 1994, Qualifying tournament, Group 1 |
 | 25.01.1994 |  | Grenada | | Puerto Rico |  | 2:0 aet (0:0) |
| Bridgetown |
Caribbean Cup 1994, Qualifying tournament, Group 1 |
 | 23.01.1994 |  | Barbados | | Puerto Rico |  | 0:1 |
| Bridgetown |
Caribbean Cup 1993, Final tournament, Group A |
 | 25.05.1993 |  | Jamaica | | Puerto Rico |  | 1:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
 | 23.05.1993 |  | Saint Kitts and Nevis | | Puerto Rico |  | 1:0 |
| Kingston |
Caribbean Cup 1993, Final tournament, Group A |
 | 21.05.1993 |  | Puerto Rico | | Sint Maarten |  | 3:0 |
| Kingston |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 14.03.1993 |  | Puerto Rico | | Cayman Islands |  | 4:0 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 12.03.1993 |  | Guyana | | Puerto Rico |  | 0:2 |
| Georgetown |
Caribbean Cup 1993, Qualifying tournament, Group 2 |
 | 11.03.1993 |  | Puerto Rico | | Barbados |  | 1:0 |
| Georgetown |
Caribbean Cup 1991, Qualifying tournament, Group 1 |
 | 09.03.1991 |  | Puerto Rico | | Dominican Republic |  | 1:3 |
| San Juan |
Caribbean Cup 1991, Qualifying tournament, Group 1 |
 | 07.03.1991 |  | Puerto Rico | | Haiti |  | 2:3 |
| San Juan |