Due to the heavy volcanic activity on the island since 1995, the team has only played a handful of matches, and most of those have been away from home. Their only victories were against neighboring Anguilla in the qualifying tournament of the 1995 Caribbean Cup, winning 3–2 at home and 1–0 away. Apart from one other draw against Anguilla, all their other matches before 2018 have been lost. Since then, however, Montserrat has proven more competitive.