CFU Club Championship 2012, 3rd place match |
 | 21.06.2012 |  | Antigua Barracuda | – | Puerto Rico Islanders |  | 0:2 (0:1) |
| Trinidad and Tobago, Marabella |
CFU Club Championship 2012, Semifinal |
| 19.06.2012 |  | Williams Connection | – | Puerto Rico Islanders | | 4:1 (1:0) |
| Marabella |
CFU Club Championship 2012, Second round, group 4 |
| 25.05.2012 |  | George Town | – | Puerto Rico Islanders | | 0:8 (0:5) |
| George Town |
CFU Club Championship 2012, Second round, group 4 |
| 21.05.2012 | | Puerto Rico Islanders | – | Caledonia | | 0:0 |
| George Town |
CFU Club Championship 2011, Final |
| 29.05.2011 | | Puerto Rico Islanders | – | Tempête |  | 3:1 aet
(1:1, 1:1) |
| Guyana, Providence |
CFU Club Championship 2011, Semifinal |
| 25.05.2011 |  | Alpha United | – | Puerto Rico Islanders | | 1:3 aet
(1:1, 1:1) |
| Providence |
CFU Club Championship 2011, Round 2 |
| 14.05.2011 | | Puerto Rico Islanders | – | Walking Boys |  | 7:0 (5:0) |
| Bayamón |
CFU Club Championship 2011, Round 2 |
| 07.05.2011 | | Walking Boys | – | Puerto Rico Islanders | | 1:1 (0:0) |
| Paramaribo |
CFU Club Championship 2010, Final Round |
| 09.05.2010 | | San Juan Jabloteh | – | Puerto Rico Islanders | | 0:1 (0:1) |
| Tunapuna |
CFU Club Championship 2010, Final Round |
| 07.05.2010 | | Joe Public | – | Puerto Rico Islanders | | 1:1 (0:0) |
| Tunapuna |
CFU Club Championship 2010, Final Round |
| 05.05.2010 | | Puerto Rico Islanders | – | Bayamon | | 3:0 (2:0) |
| Tunapuna |
CFU Club Championship 2010, Round 2, group E |
| 18.04.2010 | | Puerto Rico Islanders | – | Racing | | 3:0 (2:0) |
| Bayamón |
CFU Club Championship 2010, Round 2, group E |
| 16.04.2010 | | Racing | – | Puerto Rico Islanders | | 0:2 (0:2) |
| Bayamón |
CFU Club Championship 2009, Final |
| 17.05.2009 | | Williams Connection | – | Puerto Rico Islanders | | 2:1 (2:1) |
| Tunapuna |
CFU Club Championship 2009, Semifinal |
| 15.05.2009 | | Tempete | – | Puerto Rico Islanders | | 0:2 aet
(0:0, 0:0) |
| Trinidad and Tobago, Tunapuna |
CFU Club Championship 2007, 3rd place play-off |
| 25.05.2008 | | San Juan Jabloteh | – | Puerto Rico Islanders | | 0:0 |
| Port of Spain |
CFU Club Championship 2007, 3rd place play-off |
| 10.05.2008 | | Puerto Rico Islanders | – | San Juan Jabloteh | | 1:0 (1:0) |
| Bayamón |
CFU Club Championship 2007, Semifinal |
| 14.11.2007 | | Puerto Rico Islanders | – | Joe Public | | 0:1 (0:1) |
| Trinidad and Tobago, Tunapuna |
CFU Club Championship 2007, Quarterfinal |
| 11.11.2007 | | Puerto Rico Islanders | – | Leo Victor | | 7:1 (3:0) |
| Trinidad and Tobago, Tunapuna |
CFU Club Championship 2007, Group C |
| 08.11.2007 | | Puerto Rico Islanders | – | Inter Moengotapoe | | 5:2 (3:1) |
| Couva |
CFU Club Championship 2007, Group C |
| 06.11.2007 | | Puerto Rico Islanders | – | SAP | | 10:0 (4:0) |
| Marabella |
CFU Club Championship 2007, Group C |
| 04.11.2007 |  | Harbour View | – | Puerto Rico Islanders | | 2:2 (1:2) |
| Marabella |
CFU Club Championship 2006/07, Group C |
| 13.12.2006 | | Puerto Rico Islanders | – | Williams Connection | | 0:1 (0:1) |
| Bayamón |
CFU Club Championship 2006/07, Group C |
| 09.12.2006 | | Puerto Rico Islanders | – | Hoppers | | 3:1 (3:1) |
| Bayamón |
