Jamaica's home matches have been played at Independence Park since its opening in 1962 Their sole appearance in the FIFA World Cup was in 1998, where the team finished third in its group and failed to advance.

Jamaica also competes in the CONCACAF Gold Cup, appearing thirteen times and finishing twice as runners-up to Mexico in 2015 and the United States in 2017.

[7] From 1925 to 1962, Jamaica had regular games with teams from Trinidad and Tobago, Haiti, and Cuba, as well as with clubs like the Haitian Racing CH and Violette AC, the British Corinthians, and the Argentinean Tigers.

[4] At the 1962 Central American and Caribbean Games played in Jamaica, the national team was led by Brazilian coach Jorge Penna.

[11] A year later, Jamaica competed in the first CONCACAF Championship in El Salvador, where the team finished last in its group, which included Mexico, the Netherlands Antilles, and eventual winner Costa Rica.

After finishing first in its preliminary group that included Cuba and the Netherlands Antilles; Jamaica faced Costa Rica and Mexico in the final round, where the winner would qualify for the World Cup.

Jamaica then lost 7–0 to Costa Rica and ended with a draw at home in the return match, ultimately finishing with a single point.

After defeating Puerto Rico 3–1 on aggregate in the preliminary round, Jamaica played the United States for a spot in the finals.

[10] In 1990, Carl Brown was signed as head coach and led Jamaica into qualifying for the 1990 Caribbean Cup, finishing tied for third place after the final round was abandoned due to Tropical Storm Arthur.

[28] In 1997, Simões, by then promoted to head coach, scouted for players in England that had Jamaican heritage to join the national team.

Paul Hall, Fitzroy Simpson, Deon Burton and Robbie Earle were all named in the squad due their heritage.

After a 0–0 draw against Mexico, Jamaica secured its qualification and made its first-ever World Cup appearance, and the following day was declared a national holiday.

After finishing first in its group, Jamaica won the final 2–1 against Trinidad and Tobago, with goals from Oneil McDonald and Dean Sewell.

[39] In the 2002 FIFA World Cup qualification semi-finals, Jamaica faced Honduras, El Salvador, and Saint Vincent and the Grenadines in the second group.

[44] After reaching the final with wins against Saint Lucia and French Guiana, Jamaica claimed its third title and a spot at the Gold Cup.

[45] At the Gold Cup, Jamaica reached the quarter-finals before losing to the US 3–1 in Foxborough, with American player DaMarcus Beasley scoring two goals.

With coach Theodore Whitmore, Jamaica secured three wins from its remaining matches, jumping from 116th[A] to 83rd place in the world rankings.

[53] After finishing first in its group, Jamaica won against Grenada in the semi-finals, then defeating first-time finalists Guadeloupe in a penalty shoot-out.

[54][55] In the 2011 CONCACAF Gold Cup, Jamaica finished first in its group, beating Grenada 4–0, Guatemala 2–0, and Honduras 1–0 before being eliminated by the US, with goals from American players Jermaine Jones and Clint Dempsey.

"[66] A few weeks later in the 2015 Gold Cup, Jamaica finished first in its group and defeated Haiti in the quarter-finals with a goal from Giles Barnes to qualify for the semi-finals for the first time since 1998.

[67] In the semi-final, Jamaica defeated the US 2–1 with goals from Darren Mattocks and Giles Barnes, reaching its first-ever Gold Cup final.

[70] In the fourth round, Jamaica started off strong with a 1–0 win over Haiti and a 1–1 draw with Costa Rica, earning four points after three games.

[76] In the final against the US, Jamaica conceded the opening goal at the end of the first half before Je-Vaughn Watson tied the score in the 50th minute.

[81] On 21 November 2023, Jamaica qualified for the 2024 Copa América by reaching the 2023–24 CONCACAF Nations League A semifinals on a 3–2 comeback against Canada.

[94][95] After another three-year contract with Kappa between 2012 and 2014,[96] the JFF signed a four-year deal with Emirati sportswear company Romai Sports for US$4.8 million.

[107] The second match against Argentina saw Gabriel Batistuta getting a second half hat-trick, aiding in Jamaica's second defeat and elimination from the World Cup.

[65] The following year, the team competed in the Copa América Centenario as winners of the 2014 Caribbean Cup, again finishing last in the group stage following a 3–0 loss to Uruguay.

[64][73] Jamaica qualified for the 2024 Copa América by reaching the 2024 CONCACAF Nations League Finals, but again exited in the group stage with no points.

[109] Jamaica's highest winning margin is twelve goals, which has been achieved on two occasions: against the British Virgin Islands in 1994 (12–0) and against Saint Martin in 2004 (12–0).