CFU Club Championship 2020, Group B |
 | 09.02.2020 |  | Portmore United | – | Arcahaie |  | 0:1 (0:0) |
| Kingston |
CFU Club Championship 2020, Group B |
| 05.02.2020 | | Portmore United | – | Atlético Pantoja |  | 0:4 (0:2) |
| Kingston |
CFU Club Championship 2019, Final Round |
| 16.05.2019 | | Portmore United | – | Waterhouse | | 1:1 (1:0) |
| Kingston Stadium East |
CFU Club Championship 2019, Final Round |
| 14.05.2019 | | Capoise | – | Portmore United | | 0:1 (0:0) |
| Kingston Stadium East |
CFU Club Championship 2019, Final Round |
| 12.05.2019 | | Portmore United | – | Real Hope | | 1:0 (1:0) |
| Kingston Stadium East |
CFU Club Championship 2018, 3rd place match |
| 13.05.2018 | | Portmore United | – | Central |  | 2:1 (0:1) |
| Kingston |
CFU Club Championship 2018, Semifinal |
| 11.05.2018 | | Atlético Pantoja | – | Portmore United | | 4:3 (3:2) |
| Kingston |
CFU Club Championship 2018, Group B |
| 11.02.2018 | | Portmore United | – | Racing | | 0:1 (0:1) |
| Santiago de los Caballeros |
CFU Club Championship 2018, Group B |
| 09.02.2018 | | Atlántico | – | Portmore United | | 2:2 (0:1) |
| Santiago de los Caballeros |
CFU Club Championship 2018, Group B |
| 07.02.2018 | | Central | – | Portmore United | | 0:2 (0:0) |
| Santiago de los Caballeros |
CFU Club Championship 2017, 3rd place match |
| 21.05.2017 | | Central | – | Portmore United | | 2:2 aet
(1:1, 2:2),
pen. 3:5 |
| Port of Spain |
CFU Club Championship 2017, Final Round, Group B |
| 18.05.2017 | | San Juan Jabloteh | – | Portmore United | | 2:2 (2:0) |
| Port of Spain |
CFU Club Championship 2017, Final Round, Group B |
| 16.05.2017 | | Portmore United | – | Racing | | 1:0 (1:0) |
| Port of Spain |
CFU Club Championship 2017, Group D |
| 18.03.2017 | | Portmore United | – | Transvaal |  | 6:1 (3:0) |
| Bayamón |
CFU Club Championship 2017, Group D |
| 16.03.2017 |  | Puerto Rico | – | Portmore United | | 0:1 (0:0) |
| Bayamón |
CFU Club Championship 2017, Group D |
| 14.03.2017 |  | Scholars International | – | Portmore United | | 0:2 (0:2) |
| Bayamón |
CFU Club Championship 2013, Play-off |
| 22.05.2013 | | Caledonia | – | Portmore United | | 2:2 (1:0) |
| Couva |
CFU Club Championship 2013, Play-off |
| 20.05.2013 | | Portmore United | – | Caledonia | | 0:1 (0:1) |
| Port of Spain |
CFU Club Championship 2013, Group 2 |
| 30.04.2013 | | Portmore United | – | Bayamon | | 5:0 (1:0) |
| Kingston |
CFU Club Championship 2013, Group 2 |
| 28.04.2013 | | Portmore United | – | Valencia | | 3:4 (0:3) |
| Kingston |
CFU Club Championship 2013, Group 2 |
| 26.04.2013 | | Portmore United | – | Boys' Town | | 1:0 (0:0) |
| Kingston |
CFU Club Championship 2007, Quarterfinal |
| 11.11.2007 | | Portmore United | – | Harbour View | | 0:2 (0:1) |
| Trinidad and Tobago, Marabella |
CFU Club Championship 2007, Group D |
| 08.11.2007 | | Portmore United | – | Leo Victor | | 3:0 (2:0) |
| Tunapuna |
CFU Club Championship 2007, Group D |
| 04.11.2007 | | Portmore United | – | Helenites |  | 2:0 (1:0) |
| Tunapuna |
CFU Club Championship 2005, Final |
| 11.12.2005 | | Portmore United | – | Robin Hood | | 4:0 (1:0) |
| Suriname, Paramaribo |
CFU Club Championship 2005, Final |
| 09.12.2005 | | Robin Hood | – | Portmore United | | 2:1 (0:0) |
| Paramaribo |
CFU Club Championship 2005, Semifinal |
| 03.12.2005 | | Portmore United | – | Barber |  | 0:1 (0:0) |
| Netherlands Antilles, Marabella |
CFU Club Championship 2005, Semifinal |
| 30.11.2005 | | Barber | – | Portmore United | | 1:3 (1:2) |
| Marabella |
CFU Club Championship 2005, Quarterfinal |
| 16.10.2005 | | Portmore United | – | Hoppers |  | 7:0 (2:0) |
| Antigua and Barbuda, Greenbay |
CFU Club Championship 2005, Quarterfinal |
| 14.10.2005 | | Hoppers | – | Portmore United | | 0:3 (0:1) |
| Greenbay |
CFU Club Championship 2003, Round 3 |
| 28.11.2003 | | Williams Connection | – | Portmore United | | 1:0 (1:0) |
| Marabella |
CFU Club Championship 2003, Round 2 |
| 12.11.2003 | | Barber | – | Portmore United | | 1:2 (0:1) |
| Barber |
CFU Club Championship 2003, Round 2 |
| 05.11.2003 | | Portmore United | – | Barber | | 1:0 (1:0) |
| Portmore |
CFU Club Championship 2003, Round 3 |
| 05.11.2003 | | Portmore United | – | Williams Connection | | 0:0 |
| Trinidad and Tobago, Marabella |
CFU Club Championship 2003, Round 1 |
| 15.10.2003 |  | Pointe Michel | – | Portmore United | | -:+ |
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