Head to Head
| Central America - World Cup Qualifying | 2021/10/10 22:00 | Jamaica v Canada | D | 0-0 |
| International Match | 2017/09/02 23:00 | Canada v Jamaica | W | 2-0 |
| CONCACAF Gold Cup | 2017/07/20 23:30 | Jamaica v Canada | L | 2-1 |
| CONCACAF Gold Cup | 2015/07/11 22:30 | Jamaica v Canada | L | 1-0 |
| African Nations C'ship Qualifying | 2014/09/09 23:30 | Canada v Jamaica | W | 3-1 |
Home History
| North & Central America - World Cup Qualifying | 2022/03/25 02:05 | Costa Rica v Canada | L | 1-0 |
| North & Central America - World Cup Qualifying | 2022/02/03 02:00 | El Salvador v Canada | W | 0-2 |
| North & Central America - World Cup Qualifying | 2022/01/30 20:05 | Canada v USA | W | 2-0 |
| North & Central America - World Cup Qualifying | 2022/01/28 01:05 | Honduras v Canada | W | 0-2 |
| Central America - World Cup Qualifying | 2021/11/17 02:05 | Canada v Mexico | W | 2-1 |
| Central America - World Cup Qualifying | 2021/11/13 02:05 | Canada v Costa Rica | W | 1-0 |
| Central America - World Cup Qualifying | 2021/10/13 23:30 | Canada v Panama | W | 4-1 |
| Central America - World Cup Qualifying | 2021/10/10 22:00 | Jamaica v Canada | D | 0-0 |
Away History
| North & Central America - World Cup Qualifying | 2022/03/24 23:05 | Jamaica v El Salvador | D | 1-1 |
| North & Central America - World Cup Qualifying | 2022/02/03 00:00 | Jamaica v Costa Rica | L | 0-1 |
| North & Central America - World Cup Qualifying | 2022/01/30 22:05 | Panama v Jamaica | L | 3-2 |
| North & Central America - World Cup Qualifying | 2022/01/28 00:00 | Jamaica v Mexico | L | 1-2 |
| International Match | 2022/01/21 01:00 | Peru v Jamaica | L | 3-0 |
| Central America - World Cup Qualifying | 2021/11/16 22:00 | Jamaica v USA | D | 1-1 |
| Central America - World Cup Qualifying | 2021/11/13 02:00 | El Salvador v Jamaica | D | 1-1 |
| Central America - World Cup Qualifying | 2021/10/14 00:05 | Honduras v Jamaica | W | 0-2 |