|QUALIFICATION METHOD||Runners-up of the 2019–20 Concacaf Nations League, League B (Group B).|
|PREVIOUS APPEARANCES||1st (2021)|
Perhaps no team has captured the imagination of fans around the region in recent years than Montserrat. The nation with the smallest population in Concacaf, Montserrat came within a whisker of qualifying for the 2019 Gold Cup when they finished with a 3W-0D-1L record in CNL Qualifying. The Emerald Boys followed that up with a second-place finish in Group B of League B of the 2019-20 CNL. The staple of Montserrat is a well-organized defense that gave up just five goals in six CNL matches. That solid structure in the back could yield big results in the Prelims and a first ever Gold Cup berth.