Sint Maarten returned to international football in 2016, entering 2017 Caribbean Cup qualification and being drawn into Group 2 along with Grenada national football team and the United States Virgin Islands national soccer team with the first round matches taking place on 22 and 26 March 2016. Sint Maarten had been absent from senior CFU competition for nineteen years as they entered the tournament. In January 2016 it was announced that Sint Maartens squad for 2017 Caribbean Cup qualification would be composed solely of players from Flames United SC, reigning champions from the 2014/2015 Senior league competitions and the champions of the 2012/2013 Excellence Division between the islands of Sint Maarten, Saint Martin and St. Barths. However, shortly thereafter it was reported that the previous report was inaccurate and that Flames United would actually be competing in the CFU Club Championship. Sint Maarten played its first senior mens international in 12 years on 13 March 2016 as it hosted a 2–0 home victory against Anguilla national football team as part of each sides preparation for 2017 Caribbean Cup qualification. Both of Sint Maartens goals were scored by Joost Röben. In the first match of the tournament, Sint Maarten held Grenada to a scoreless draw in the first half which saw two of Sint Maartens starters sustain injuries. It was later revealed that Raymond Wolff had sustained a broken rib before coming off in the first half while fellow-Dutchman Rick De Punder was credited with an own goal. Grenada scored five goals in the second half to secure the 5–0 victory. Sint Maarten arrived on Grenada for the 8pm match at 4pm after the funds for the team airfare, paid for by the CFU, did not reach the airline in time and no seats were available. SMSA President Johnny Singh thought that the team would not be able to compete but another flight was arranged in time. The same scenario occurred for the return flight but the team was expected to be home on the Thursday prior to the teams match against USVI on Saturday. Sint Maarten went on to lose the match to USVI 1–2, ending the teams qualifying campaign. Sint Maartens only goal was scored by Ramsleii Boelijn.

How many days apart were the first round matches in the US Virgin Islands?
4