CFU Club Championship 2014, Group 2 |
| 25.03.2014 | | Caledonia | | Waterhouse | | 0:4 (0:1) |
| Mirebalais |
CFU Club Championship 2014, Group 2 |
| 23.03.2014 | | Inter Moengotapoe | | Caledonia | | 2:2 (0:0) |
| Mirebalais |
CFU Club Championship 2014, Group 2 |
| 21.03.2014 | | Mirebalais | | Caledonia | | 0:3 (0:2) |
| Mirebalais |
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 1 |
| 28.04.2013 | | Caledonia | | Antigua Barracuda | | 3:1 (2:0) |
| Couva |
CFU Club Championship 2013, Group 1 |
| 26.04.2013 | | Williams Connection | | Caledonia | | 4:0 (2:0) |
| Couva |
CFU Club Championship 2012, Final |
| 21.06.2012 | | Caledonia | | Williams Connection | | 1:1 aet (0:0), pen. 4:3 |
| Marabella |
CFU Club Championship 2012, Semifinal |
| 19.06.2012 | | Caledonia | | Antigua Barracuda | | 2:0 (0:0) |
| Marabella |
CFU Club Championship 2012, Second round, group 4 |
| 23.05.2012 | | Caledonia | | George Town | | 5:0 (0:0) |
| 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, Round 2 |
| 08.05.2011 | | Tempête | | Caledonia | | 0:1 (0:1), pen. 3:2 |
| Saint-Marc |
CFU Club Championship 2011, Round 2 |
| 22.04.2011 | | Caledonia | | Tempête | | 0:1 (0:1) |
| Couva |
CFU Club Championship 2011, Round 1 |
| 19.03.2011 | | Caledonia | | Newtown United | | 5:0 (2:0) |
| Port of Spain |
CFU Club Championship 2011, Round 1 |
| 10.03.2011 | | Newtown United | | Caledonia | | 0:1 (0:0) |
| Bassterre |
CFU Club Championship 1998, Final |
| 28.11.1998 | | Joe Public | | Caledonia | | 1:0 (1:0) |
| |
CFU Club Championship 1998, Semifinal |
| 25.11.1998 | | Caledonia | | Aiglon du Lamentin | | 4:3 |
| |
CFU Club Championship 1998, Quarterfinal |
| 20.11.1998 | | Caledonia | | Chelsea | | 13:0 |
| |