Barry started his career within the youth ranks at Brighton & Hove Albion before signing a development contract with them in 2013.[3] However, Barry suffered a leg injury that kept him sidelined for 11 months.[4] After recovering from his leg injury, Barry returned to development squad and played his first match, as well as captain, against Blackburn Rovers U21 on 18 August 2014.[5]
Barry was released by 'the Seagulls' in the summer of 2015 without making a single appearance for the senior side.[6]
Swindon Town
Preceding his release from Brighton, Barry joined League One side Swindon Town on a one-year deal following a successful trial.[7]
On 1 September 2015, Barry went onto make his Swindon debut in their Football League Trophy victory over Newport County, featuring for the full 90 minutes.[8] Four days later, Barry made his league debut for the club in their 3–1 away victory against Crewe Alexandra, once again featuring for the entire 90 minutes.[9] Despite suffering setback of injuries,[10][11] Barry went onto make thirty-four more league starts for Swindon before signing a new one-year deal alongside teammate Ellis Iandolo in July 2016.[12]
In the 2016–17 season, on 20 August 2016, Barry scored his first goal for Swindon, netting the winner in their 1–0 victory over Port Vale in the 47th minute.[13] However, Barry's first team opportunities was soon limited with injuries[14][15] and suspension, which has affected his season.[16][17] Despite this, Barry went on to make twenty-six appearances and scoring once in all competitions.
On 2 May 2017, it was announced that Barry would leave Swindon upon the expiry of his contract in June 2017.[18]
Chesterfield
On 18 May 2017, Barry signed a two-year deal with Chesterfield.[19] He was loaned out to Dover Athletic in September 2018. After missing six games for Dover and amidst an injury crisis at Chesterfield, he was recalled early in November.[20]
Barry left the club in May 2019, at the expiry of his contract.[21]
Barrow
Shortly after his exit from Chesterfield, Barry signed a two-year deal at Barrow, also in the National League.[22] In his first season he formed part of the side that won promotion to League Two.[23]
Stevenage
Barry signed for fellow League Two club Stevenage on 8 July 2021.[24]