Antigua and Barbuda

First official international match

On November 10, 1972, Antigua and Barbuda's first official match was in the 1973 CONCACAF Championship qualification, losing to Trinidad and Tobago 11–1 in Port of Spain, which is the worst defeat in the team's history.

Friendlies against European teams

On 17 December 2005, the Antigua and Barbuda national team played their first match against a European opponent after the Hungarian Football Federation invited "the Benna Boys" to play Hungary in an international friendly at Lockhart Stadium in Fort Lauderdale, Florida. This was the first match coached by former national striker Derrick Edwards. Hungary defeated Antigua and Barbuda 3–0.

On 2 May 2016, the Estonian Football Association announced that their national team would play Antigua and Barbuda in an international friendly on 22 November. It was the team's second match against a European opponent. Estonia won the game 1–0.

2018 drug bust in Jamaica

During the March 2018 FIFA Calendar Antigua and Barbuda played Jamaica, drawing 1–1 away at Sabina Park, levelling in the last seconds of match from a header from Peter Byers. Upon the team's preparation for their departure back to Antigua, assistant coach Derrick Edwards and equipment manager Danny Benjamin were arrested and charged with possession of, dealing in, and taking steps to export marijuana, and conspiracy at the Norman Manley International Airport. Initially, Edwards was awarded bail and Benjamin was held without bail; after a month, both Edwards and Benjamin were placed under house arrest and curfew and gave up their travel documents. Both men were acquitted of the crime on 14 June, citing there was not enough evidence to prove their involvement in the carrying the drugs with the intention of smuggling them out of Jamaica.