[5] 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.

[3][4] Many of the games were played at Sabina Park and many clubs were established, including Melbourne, Kingston, Kensington, Lucas and St George's Old Boys.

[3] In 1965, under the leadership of Brazilian coach Jorge Penna, Jamaica made its first attempt at World Cup qualifying.

In the away games Jamaica was held to a goalless draw with the Netherlands Antilles and suffered a 2–1 defeat to Cuba.

[7] Jamaica's participation in the 1974 World Cup elimination saw the suspension of 17 players on the team because of poor behaviour on a tour to Bermuda.

In 1982 Jamaica did not make an attempt for the World Cup Final set in Spain due to insufficient funds and a poorly prepared team.

In qualifying, Jamaica beat Puerto Rico 2–1 and was then faced with Bermuda, Canada, and El Salvador from which two teams would advance to the final round.

Under Brazilian Professor Renê Simões and National coach Carl Brown, Jamaica became a powerhouse in the Caribbean region and received the "Best Mover" award by FIFA in 1996.