Head to Head
| CONCACAF Gold Cup | 2021/07/20 23:00 | Costa Rica v Jamaica | W | 1-0 |
| International Match | 2019/03/27 02:00 | Costa Rica v Jamaica | W | 1-0 |
| Central America - World Cup Qualifying | 2016/03/30 02:00 | Costa Rica v Jamaica | W | 3-0 |
| Central America - World Cup Qualifying | 2016/03/26 00:00 | Jamaica v Costa Rica | D | 1-1 |
| CONCACAF Gold Cup | 2015/07/09 00:00 | Costa Rica v Jamaica | D | 2-2 |
Home History
| Central America - World Cup Qualifying | 2021/09/05 23:00 | Costa Rica v Mexico | L | 0-1 |
| Central America - World Cup Qualifying | 2021/09/03 01:05 | Panama v Costa Rica | D | 0-0 |
| International Match | 2021/08/22 03:00 | El Salvador v Costa Rica | D | 0-0 |
| CONCACAF Gold Cup | 2021/07/25 23:00 | Costa Rica v Canada | L | 0-2 |
| CONCACAF Gold Cup | 2021/07/20 23:00 | Costa Rica v Jamaica | W | 1-0 |
| CONCACAF Gold Cup | 2021/07/17 00:30 | Suriname v Costa Rica | W | 1-2 |
| CONCACAF Gold Cup | 2021/07/13 01:00 | Costa Rica v Guadeloupe | W | 3-1 |
| International Match | 2021/06/09 23:00 | USA v Costa Rica | L | 4-0 |
Away History
| Central America - World Cup Qualifying | 2021/09/05 22:00 | Jamaica v Panama | L | 0-3 |
| Central America - World Cup Qualifying | 2021/09/03 02:00 | Mexico v Jamaica | L | 2-1 |
| CONCACAF Gold Cup | 2021/07/26 01:30 | USA v Jamaica | L | 1-0 |
| CONCACAF Gold Cup | 2021/07/20 23:00 | Costa Rica v Jamaica | L | 1-0 |
| CONCACAF Gold Cup | 2021/07/16 22:30 | Guadeloupe v Jamaica | W | 1-2 |
| CONCACAF Gold Cup | 2021/07/12 22:30 | Jamaica v Suriname | W | 2-0 |
| International Match | 2021/06/07 07:00 | Serbia v Jamaica | D | 1-1 |
| International Match | 2021/03/25 17:00 | USA v Jamaica | L | 4-1 |