Clare born Barry signed for Limerick in August 2015, and managed to break into the first team in 2017. He made 11 appearances during the first half of the 2017 League of Ireland season. Barry transferred to Ipswich Town in January 2018, making his first-team debut that April. He subsequently spent two seasons on loan at Chelmsford City.
Barry joined the Hoops in August 2021, making his debut against Finn Harps with an impressive performance at left wing back and has followed it up with a number of excellent displays and appears to be developing a real affinity with the club.
In July 2022, Barry joined St. Patrick’s Athletic on loan until the end of the 2022 seaon.