[3] They participated in the Leeward Islands Tournament from 1949 however had to wait until 1979 to play their first official matches, in the qualifying rounds for the 1979 CFU Championship, losing twice to Jamaica, both results finishing 2–1.

[citation needed] They would again fail to qualify for the final phase of the 1983 CFU Championship after advancing due to Jamaica's withdrawal, eliminated by Martinique, who won 12–0 on aggregate.

[citation needed] Saint Kitts and Nevis finished bottom of their group in 1996 but in the 1997 Caribbean Cup, they advanced into the knock-out after finishing level on points with both Trinidad and Tobago and Martinique, then defeated Grenada 2–1 in extra-time with both goals scored by Keith Gumbs, but they succumbed to Trinidad and Tobago 0–4 in the final.

[citation needed] In the 2002 World Cup qualifiers, after comfortably beating the Turks and Caicos Islands with an aggregate result of 14–0, Saint Vincent and the Grenadines once again dispatched the Sugar Boyz, winning both in Kingstown (1–0) as in Basseterre (1–2).

[citation needed] However, the situation would improve in the 2006 qualifiers, since Saint Kitts and Nevis advanced to the second group phase after leaving the US Virgin Islands and Barbados on the way.

[citation needed] They shared Group 3 with Mexico, Trinidad and Tobago and Saint Vincent and the Grenadines, but as expected, finished in last place, with 6 losses in as many appearances.

[citation needed] In the preliminary round for the 2010 qualifiers, they were unable to repeat what they had done four years ago and were unceremoniously eliminated by Belize, who won 4–2 on aggregate.

[citation needed] St. Kitts and Nevis continues its pattern of international tours and travels in August 2017 to Mumbai to meet Mauritius and India in a friendly tournament, the 2017 Hero Tri-Nation Series.