Puerto Rico's first international match was against Cuba in 1940 in which they drew 1–1. They did not record a win until a 3–0 result in 1970 against the Bahamas. In 1972 Puerto Rico recorded a 1–0 win against Panama in a friendly. Wins between the '80s and '90s were mainly against the Bahamas, the Dominican Republic, and Martinique.
Chris Armas played for Puerto Rico in the 1993 Caribbean Cup. In the tournament Puerto Rico established a 4 game win streak without conceding a goal. The competition was not then recognized by FIFA and so his five matches were considered friendlies. As a result, he was later allowed to switch his allegiance to the United States of America, for whom he has since been capped over fifty times.
Over the past few years Puerto Rico has begun to emerge as a contender, like they were in the 1990s. In 2008, they drew with the Caribbean giants Trinidad and Tobago. They also won for the first time since 1994 when they beat the Dominican Republic in the first round of World Cup qualifiers. Although they lost the first leg 4–0 to Central American powerhouse Honduras, they fought a 2–2 tie in the home leg in the second round. The Puerto Rican Football Federation has announced plans that would allow them to participate in the next editions of the Caribbean Cup and Gold Cup.