They were the first Caribbean team to make the World Cup, which they did in 1938. There, they defeated Romania in a replay 2–1 after drawing against them 3–3. They were then eliminated in the quarter-finals by Sweden, 8–0. Cuba has not returned to the World Cup since.
Cuba played its first international football match on 16 March 1930 at that year's Central American and Caribbean Games. They beat Jamaica (then a British colony) 3–1 in Havana. Four days later they beat Honduras 7–0. Cuba were managed by José Tapia, who remained in charge until after Cuba's 1938 FIFA World Cup campaign. Cuba's first World Cup qualification campaign was for the 1934 FIFA World Cup in Italy. All of the CONCACAF entrants were placed in Group 11. The winner of a best-of-three tournament between the two weakest nations, Cuba and Haiti would produce a winner to play 1930 qualifiers Mexico in another round of best-of-three. The winner of that would play 1930 semi-finalists the United States of America for a place in the finals. All of the matches between Cuba and Haiti in the first round were staged at Parc Leconte in Port-au-Prince, Haiti, on 28 January, 1 February and 4 February 1934. Cuba won the first match 3–1 with Mario Lopez opening from a penalty and Hector Socorro scoring the second. The second match was a 1–1 draw with Lopez equalising in the 85th minute. In the final match Cuba won 6–0 with two Lopez goals, one from Hector Socorro and one from his brother Francisco. The second round against Mexico consisted of three matches at Parque Necaxa in Mexico City. Its first match, on 4 March 1934, saw Mexico go 3–0 up with a hat-trick by Dionisio Mejia, his goals scored in the 12th, 14th and 16th minutes. Mario Lopez scored twice for Cuba with one in each half, but Mexico won 3–2. A week later Mejia scored another hat-trick as Mexico won 5–0, and seven days later Mexico won 4–1 after Lopez opened the scoring in the 15th minute. Mexico did not qualify, their 4–2 play-off defeat to the United States was held in Rome during the finals, as the two teams had forgotten to stage it earlier
The decision to stage the 1938 World Cup in France was poorly received in the Americas, who had hoped for it to return to South America after the 1934 World Cup in Italy. All nations in South America except Brazil withdrew, and all CONCACAF nations except Cuba, thus the two qualified by default. The tournament was held as a straight knock-out tournament of 16 nations. Cuba were drawn to play their first-ever World Cup finals match against Romania (who were making their third finals appearance) at Stade Chapou in Toulouse, on 5 June 1938. Silviu Bindea put Romania ahead after 35 minutes and Hector Socorro equalised nine minutes later. With three minutes remaining Tomas Fernandez gave Cuba the lead, but within a minute Iuliu Baratky forced extra time with a Romanian equaliser. Romania went 3–2 up in extra-time by Stefan Dobay's goal on 105 minutes, but Juan Tunas equalised for Cuba with three minutes of extra-time remaining. The replay was held at the same stadium, on 9 June. This was at the same time as Switzerland's 4–2 replay win over Germany. Dobay put Romania 1–0 up at half-time with a 35th minute goal, but in the second half Cuba equalised through Socorro in the 51st minute. Six minutes later, Carlos Oliviera scored the winning goal and it ended 2–1. In the quarter-final Cuba lost 8–0 to Sweden at Stade du Fort Carre in Antibes, on 12 June. Sweden's Tore Keller and Gustav Wetterstrom each scored hat-tricks.
The NAFC Championship 1949 served as CONCACAF's qualification group for the 1950 FIFA World Cup in Brazil. Cuba, the United States of America and Mexico played each other twice in a tournament held in Mexico City in September 1949. The top two would qualify. Cuba came third and did not qualify, their only point was gained from their second match, a 1–1 draw against the United States on 14 September. Cuba did not compete in World Cup qualification again until 1966. They returned to participation in qualification for 1978, but the 1982 qualifiers represented a significant breakthrough- Cuba reached the final round of qualifying, and were only 2 points short of reaching the 1982 World Cup. In recent years, Cuban football has seen an improvement in results.
They reached the Quarter-finals of the 2003 Gold Cup (where they were beaten by the USA) by defeating Canada 2–0 in the Group Stage. During the 2006 World Cup qualifiers Cuba faced Costa Rica and were only eliminated on away goals. They held Costa Rica to a draw in Havana 2–2 and later battled it out for a 1–1 draw in Costa Rica. During the 2010 World Cup qualifiers Cuba faced Antigua & Barbuda and drew 3–3 against Antigua & Barbuda. Later in Pedro Marreo Cuba won 4–1 to advance to the semifinal round of the CONCACAF World Cup Qualifiers. Cuba was with United States, Trinidad & Tobago and Guatemala. Cuba finished in the fourth place with only a victory against Guatemala 2–1 with a goal scored by Aliannis Urgellés. They finished in third place in the Caribbean Cup 2010 to take a place in Gold Cup 2011. In 2012 Cuba won the Caribbean Cup for the first time.
For the 2014 FIFA World Cup, the Cuban team qualified directly to the Third Round as one of the six highest ranked teams and were place in Group C with Honduras, Panama, and Canada. Although the Cuban team had a couple of close games, they ended up their qualification process with 1 draw and 5 defeats (losing home and away to Canada and Honduras and drawing to Panama in Havana in their final game after losing in Panama City). Their only goal of the qualifying campaign came from Alberto Gomes against Panama in the final game of the group.