on may 21, 2016, orlando city was drawn to face the winner of the third round match between jacksonville armada fc, and the winner of the second round match between the villages sc and charleston battery. although the villages sc won the match on penalty shootout, they were subsequently disqualified for fielding an ineligible player. jacksonville armada ultimately won the third round matchup, setting up a match in jacksonville against orlando city, a rematch of their preseason match.