Montserrat

The Montserrat national team is one of the newest in international football, having played its first senior match on 10 May 1991, during the 1991 Caribbean Cup tournament. The team suffered a 3–0 defeat against Saint Lucia. The team's next match was against Anguilla; securing a 1–1 draw. Montserrat once again entered the Caribbean Cup the following year, but were once more knocked out in the group stage, with heavy defeats against Saint Kitts and Nevis and Antigua and Barbuda. They were drawn against the same two teams in the 1994 Caribbean Cup, again being eliminated in the tournament's group stage, conceding 17 goals in two matches. In 1994, the Montserrat Football Association (MFA) was formed. Like all other football teams based in the Caribbean, the MFA became a member of CONCACAF.

On 26 March 1995, Montserrat played their first ever home international match. They defeated Anguilla 3–2, thus achieving their first win. The team beat Anguilla again in the next fixture, to ensure progression to the Second Qualifying Round of the 1995 Caribbean Cup. The 1–0 win in the second leg, was their only clean sheet in international football, and their most recent victory for the next seventeen years. The side exited the competition in the next stage, losing 20–0 against Saint Vincent and the Grenadines.

Soon afterwards, the Soufrière Hills volcano became active and the eruptions destroyed Plymouth, the capital of Montserrat, severely disrupting life on the island. Despite the lack of football action, the MFA became a member of FIFA in 1996. However, it was a further three years before the Montserrat team played another match. This was mostly because many of the island's footballers had emigrated from the area, many of them to England.

After a four-year hiatus, the team entered the 1999 Caribbean Nations Cup. They were knocked out in the preliminary round of the tournament, losing 6–1 to the British Virgin Islands. Due to the volcanic activity on the island, Montserrat had been unable to enter the FIFA World Cup 1998 tournament, so their entry to the 2002 World Cup was their first; but it was not a success as they were defeated 6–1 by the Dominican Republic. In 2001, the MFA visited The Football Association to raise money for a new stadium. Shortly after this the Blakes Estate Stadium was opened. The team's next match was on 30 June 2002, the day of the World Cup Final, when Montserrat played Bhutan in a game known as "The Other Final". The friendly match between the two lowest-ranked teams in the world ended with a 4–0 win for Bhutan in front of 15,000 fans in Thimphu.

Montserrat entered the World Cup qualifiers once more for the 2006 competition, but again lost in the first qualifying round, this time losing 20–0 against Bermuda. Montserrat then competed in the 2005 Caribbean Cup, but once more failed to progress past the preliminary round. In 2008, they were defeated 7–1 by Suriname in the first qualifying round of the 2010 World Cup.

The team played a friendly match against a Network Rail XI on May 19, 2012, ending in a 4–4 draw.

Montserrat achieved their first victory since 1995 and their first ever victory since joining FIFA, beating the British Virgin Islands 7–0 in a 2012 Caribbean Championship qualifying match.

Montserrat's fortunes changed dramatically in 2018 with the arrival of Willie Donachie and the launch of the CONCACAF Nations League. The side won three of their four qualifying games, but missed out on qualification for the 2019 CONCACAF Gold Cup on goal difference. The team went on to take second place in their group in the inaugural season with two wins, draws, and losses each, thus keeping their place in the second tier.

Following Willie Donachie, in 2022 Matt Lockwood took over for a spell as head coach and technical director, supported in March 2023 by assistant coaches Craig Easton and David Preece. Just months later on September 8, Lee Bowyer took over as the Montserrat manager and Steve Gallen is the assistant. In their first game they beat Barbados with a 99th-minute winner to go second in their CONCACAF Nations League group.