CONCACAF Nations League 2023/24, League A, Quarterfinal |
 | 21.11.2023 |  | Canada | – | Jamaica |  | 2:3 (1:0) |
| Toronto |
CONCACAF Nations League 2023/24, League A, Quarterfinal |
| 18.11.2023 | | Jamaica | – | Canada | | 1:2 (0:1) |
| Kingston |
World Cup 2022, Qualifying tournament, CONCACAF, Third round |
| 27.03.2022 | | Canada | – | Jamaica | | 4:0 (2:0) |
| Toronto |
World Cup 2022, Qualifying tournament, CONCACAF, Third round |
| 10.10.2021 | | Jamaica | – | Canada | | 0:0 |
| Kingston |
Friendly internationals 2017 |
| 02.09.2017 | | Canada | – | Jamaica | | 2:0 (2:0) |
| Toronto |
CONCACAF Gold Cup 2017, Final tournament, Quarterfinal |
| 20.07.2017 | | Jamaica | – | Canada | | 2:1 (1:0) |
| Glendale |
CONCACAF Gold Cup 2015, Final tournament, Group B |
| 11.07.2015 | | Jamaica | – | Canada | | 1:0 (0:0) |
| USA, Houston |
Friendly internationals 2014 |
| 09.09.2014 | | Canada | – | Jamaica | | 3:1 (1:1) |
| Toronto |
Friendly internationals 2010 |
| 31.01.2010 | | Jamaica | – | Canada | | 1:0 (0:0) |
| Kingston |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 2 |
| 19.11.2008 | | Jamaica | – | Canada | | 3:0 (1:0) |
| Kingston |
World Cup 2010, Qualifying tournament, CONCACAF, Third round, group 2 |
| 20.08.2008 | | Canada | – | Jamaica | | 1:1 (0:0) |
| Toronto |
CONCACAF Gold Cup 2009, Final tournament, Group A |
| 03.07.2009 | | Canada | – | Jamaica | | 1:0 (0:0) |
| Carson |
Friendly internationals 2006 |
| 08.10.2006 | | Jamaica | – | Canada | | 2:1 (2:1) |
| Kingston |
Friendly internationals 2006 |
| 04.09.2006 | | Canada | – | Jamaica | | 1:0 (1:0) |
| Montréal |
Friendly internationals 1999 |
| 02.09.1999 | | Canada | – | Jamaica | | 1:0 (0:0) |
| |
World Cup 1998, Qualifying tournament, CONCACAF, Final Round |
| 07.09.1997 | | Jamaica | – | Canada | | 1:0 (0:0) |
| Kingston |
World Cup 1998, Qualifying tournament, CONCACAF, Final Round |
| 27.04.1997 | | Canada | – | Jamaica | | 0:0 |
| Burnaby |
Friendly internationals 1995 |
| 01.08.1995 | | Canada | – | Jamaica | | 3:1 (2:1) |
| |
World Cup 1994, Qualifying tournament, CONCACAF, Second round, group B |
| 01.11.1992 | | Canada | – | Jamaica | | 1:0 (0:0) |
| Toronto |
World Cup 1994, Qualifying tournament, CONCACAF, Second round, group B |
| 18.10.1992 | | Jamaica | – | Canada | | 1:1 (0:0) |
| Kingston |
CONCACAF Gold Cup 1991, Final tournament, Group A |
| 03.07.1991 | | Canada | – | Jamaica | | 3:2 (1:1) |
| Los Angeles |
Friendly internationals 1988 |
| 05.04.1988 | | Jamaica | – | Canada | | 0:4 |
| |
Friendly internationals 1985 |
| 13.03.1985 | | Jamaica | – | Canada | | 1:1 |
| |
CONCACAF Championship 1985, Qualifying tournament, First Round |
| | | Canada | – | Jamaica | | +:- |
| |
