Beginnings (1938–1990) Saint Kitts and Nevis played their first match on 18 August 1938, against
Grenada, a match that ended in a 2–4 defeat. 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. 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.
1990–2000 The
Sugar Boyz qualified for their first tournament at the
1993 Caribbean Cup, drawing against
Dominican Republic (2–2) and
British Virgin Islands (5–1) to top their qualifying group. In the tournament proper, they finished second behind
Jamaica to reach the semi-finals, before losing to
Martinique on penalties. 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. Since they'd reached the final, Saint Kitts and Nevis were entered into a play-off against
Cuba – runner-up in the
1996 Caribbean Cup – for the last ticket to the
1998 CONCACAF Gold Cup, but they lost 2–0. After benefiting from the withdrawal of the
Bahamas, they beat
Saint Lucia 5–1 in
Basseterre and 1–0 in
Castries, but fell in the third knockout round against
Saint Vincent and the Grenadines, losing thanks to the
away goals rule.
2000s 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). 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. They also experienced the worst defeat in their history, 8–0 against
Mexico. 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. In the Caribbean Cup, the
Sugar Boyz did not repeat the successes of the '90s and could only qualify to the final phase of the
2001 Caribbean Cup, although they did not advance beyond the group phase. They have not returned to a final phase since that edition.
2010–present made his debut for St. Kitts and Nevis in 2016 Qualifying directly to the second round of the
2014 qualifiers, Saint Kitts and Nevis was drawn in Group D along with
Canada,
Puerto Rico and
Saint Lucia. They finished in 3rd place, with 7 points. It was only defeated by
Canada in Toronto (4–0). In the
2018 World Cup qualifiers, Saint Kitts and Nevis defeated the
Turks and Caicos Islands in the first round by a lofty aggregate 12–4 before falling in the second phase, at the hands of
El Salvador, 6–3 on aggregate, but not before obtaining a 2–2 draw at home. In November 2015, they played 2 friendlies against European teams,
Andorra (1–0) and
Estonia (0–3).
Devaughn Elliott scored the only goal in the victory over Andorra, becoming the first St. Kitts and Nevis player to score against a European side. The result was also the first away victory for a
CFU team over a European side on their home soil. In October 2016, it reached its highest ranking in the FIFA world ranking (73rd place) thanks to its good performance in the 2nd round of the
2017 Caribbean Cup of Nations qualifiers. However, two defeats against
French Guiana (0–1) and
Haiti at home (0–2 a.e.t.) stopped the
Sugar Boyz in the 3rd round of these qualifiers. The year ends with a 1–1 draw in
Basseterre against
Estonia on November 19, 2016, in a friendly match, one year after playing against the same team in
Tallinn. In June 2017, the team went on a second European tour and played
Armenia on June 4 in
Yerevan and
Georgia three days later in
Tbilisi. Both games ended in equally bad losses, 5–0 and 3–0, respectively. The
Sugar Boyz played
Andorra again on March 25, 2022, six and a half years after their first confrontation, for a friendly match in
Andorra la Vella. This time the Principality's selection won against Saint Kitts and Nevis on its home stadium (1–0). They qualified for their first ever CONCACAF Gold Cup in
2023. ==Team image==