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 |
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