2017: Appeared in three matches as a substitute for Orlando City SC in MLS play, while he also made one start for the club in the Lamar Hunt U.S. Open Cup. Barry also made 18 appearances for Orlando City B, scoring a team-leading 10 goals and adding one assist. He tallied the game-winning goal in a 3-1 win over Toronto FC II on April 4 in his first USL appearance of the season, before tallying a goal and the game-winning assist in a 2-1 win over the Pittsburgh Riverhounds on June 3. Barry netted again the following game – a 1-1 draw with the Rochester Rhinos on June 7. After four games without a goal, Barry netted in four consecutive games from August 5 through August 19. First, he tallied in a 2-2 draw with FC Cincinnati on August 5 before adding the only goal in a 1-0 win over the Richmond Kickers on August 12. On August 16, he scored twice in a comfortable 3-0 victory over the Ottawa Fury before adding his fifth goal in four games during a 1-1 draw versus the Charlotte Independence on August 19. Barry added two more goals late in the season, netting yet another game-winner against Richmond on October 1 before finding the net for the 10th time in a wild 6-5 loss to New York Red Bulls II on October 7.
2016: Made eight appearances, including four starts, for Orlando City SC in MLS action after being selected in the first round (13th overall) in the 2016 MLS SuperDraft. He made his debut in Orlando’s season opener against Real Salt Lake on March 6, tallying an assist on Cyle Larin’s goal as Orlando fought back from two goals down to draw 2-2 with a pair of goals in stoppage time. Barry made his first start on July 16 in a 2-2 draw against Vancouver Whitecaps FC. He also started twice for the club in the Lamar Hunt U.S. Open Cup. In addition, Barry had four goals in nine appearances for Orlando City B, scoring his first two professional goals in a 2-1 win over the Rochester Rhinos on May 22. He added further goals in the 2016 USL season on June 5 against Louisville City FC and versus FC Montreal on June 25.
College: Barry played college soccer first at Monroe Community College, before transferring to the University of Central Florida ahead of his junior season. While at Monroe, Barry earned Region II Player of the Year, Championship MVP and First Team honors. In his first season at UCF, Barry scored once in 16 games before exploding in his senior season, tallying a team-leading 11 goals for the Knights.