Montserrat's fortunes changed dramatically in 2018 with the arrival of Willie Donachie and launch of the CONCACAF Nations League. The side won 3 of their four qualifying games, but missed out on qualification for the 2019 CONCACAF Gold Cup on goal difference after Nicaragua scored with 25 minutes to go against Barbados, to take the Emerald Boys' Gold Cup place. 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 at the second tier.