Puerto Rico

Early years (1940s–1980s)

Puerto Rico played its first international match against Cuba on November 12, 1940, a game that ended in a 1–1 draw. Six years later, it participated in the 1946 Central American and Caribbean Games in Barranquilla, Colombia, its first official competition. It finished in last place, suffering some embarrassing defeats, starting with a 12–0 loss to Costa Rica. Its next five games ended in defeat: 12–1 against Panama, 4–1 against the host country, Colombia, 4–1 against Guatemala, 14–0 against the Antilles, and finally, on December 26, 1946, it closed its participation with a 6–0 loss to Venezuela. In 1959, it returned to compete in the 8th edition of the regional games in Caracas. It improved slightly on its previous performance, but this was not enough to avoid finishing last, ultimately securing fifth place.

Between 1959 and 1986, Puerto Rico was a regular participant in the Central American and Caribbean Games, competing in every edition without interruption.

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. The 1970s saw Puerto Rico participate in its first World Cup qualifier, specifically for the 1974 FIFA World Cup. They were eliminated by Haiti, the eventual continental champions, who won with a resounding 12–0 aggregate score. Puerto Rico would not play in another qualifier until 1986. In the meantime, they hosted and participated in the 1979 Pan American Games in San Juan. Although they advanced from the group stage, they were unable to progress beyond the second round and finished in 5th place after the United States withdrew. They also hosted the 1981 CFU Championship, though they finished fourth and last in the final round.

Puerto Rico returned to the preliminary rounds of the FIFA World Cup for the 1986 World Cup qualifiers, where they were eliminated in a two-legged tie by El Salvador, who won 8–0 on aggregate. Also, at the 1986 edition in Santiago de los Caballeros, Dominican Republic, they reached the quarterfinals, losing 4–0 to an amateur team from Mexico.

Four years later they were eliminated again in the preliminary round of the 1990 World Cup qualifiers, although Jamaica prevailed by a less lopsided aggregate score of 3:1. Puerto Rican wins between the 1980s and 1990s were mainly against the Bahamas, the Dominican Republic, and Martinique.

1990s

The most significant event of the 1990s for the Puerto Rico team was their qualification for the final stage of the Caribbean Cup in Jamaica in 1993. Drawn in the same group as the host nation, Jamaica, along with Saint Kitts and Nevis and Sint Maarten, Puerto Rico got off to a strong start, defeating Sint Maarten 3–0. Unfortunately, they lost twice by a single goal to their other two opponents, losing any chance of reaching the tournament semifinals. Puerto Rico has not yet managed to return to the group stage of the Caribbean Cup.

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. He would later receive 66 caps for the United States.

In the 1994 World Cup qualifiers, Puerto Rico confirmed its progress, defeating the Dominican Republic in the first round (3–2 on aggregate) with a memorable 1–2 victory in Santo Domingo on March 21, 1992. In the following round, they were eliminated again by Jamaica, who won 3–1 on aggregate. In the 1998 World Cup qualifiers, they failed to replicate their previous success, suffering a crushing 9–1 defeat to Saint Vincent and the Grenadines.

Between 1995 and 2007 Puerto Rico did not record a win, and had only four draws. During this time, the team dropped down in the FIFA Rankings to 202nd.

2000s

Puerto Rico began the new century by losing to Aruba in the first round of the 2002 World Cup qualifiers (6–4 on aggregate). Four years later, they withdrew from the qualifiers for the 2006 World Cup, allowing Belize to advance in their place.

However, thanks to the participation of players in MLS and USL, the Puerto Rican national team significantly improved its level. In 2008, they won two games as visitors against Bermuda (1–0 and 2–0), and drew 2–2 with Trinidad and Tobago. They also won for the first time since 1994 when they beat the Dominican Republic in the first round of the World Cup qualifiers, although they lost the first leg 4–0 to Honduras, they fought a 2–2 tie in the home leg in the second round, and were therefore eliminated from contention.

The Puerto Rican Football Federation then announced plans that would have allowed them to participate in the next editions of the Caribbean Cup and CONCACAF Gold Cup.

Puerto Rico was supposed to make their debut in the 2010 Central American and Caribbean Games on home soil in Mayagüez, but due to the controversy of CONCACAF not approving the stadiums, the team couldn't compete in the football event. The team was supposed to play in Venezuela instead but due to the lack of teams, the male event was canceled.

2010s

In the 2014 World Cup qualifiers, Puerto Rico was placed in Group D of the first round, along with Canada, Saint Kitts and Nevis, and Saint Lucia. They finished second in the group behind Canada, with 9 points. Although that total was insufficient to advance to the second round, the Blue Hurricane earned a commendable 0–0 draw in Toronto on October 11, 2011. Many of the players on the Puerto Rican national team also played for the Puerto Rico Islanders, a team in the NASL, which at the time was the second division of American soccer.

On August 15, 2012, Puerto Rico hosted Spain, the reigning world and European champions, in a prestigious international friendly played at the Juan Ramón Loubriel Stadium in the city of Bayamón. Although the Spanish dominated the match, they only managed a narrow 2–1 victory (goals by Santi Cazorla and Cesc Fàbregas; Cintrón scored for Puerto Rico). It was the first time Puerto Rico had played against a world champion team and also Spain's first encounter with a Caribbean nation. The Spanish press was highly critical of the match.