Prior to his second season at the club, Gray was given the captain's armband by Hibs manager Alan Stubbs, taking over from Liam Craig.
[3] Gray progressed through the youth ranks up until the age of 16,[4] when he attracted the interest of Manchester United, and signed for the club for a fee of £50,000 in 2004.
[7] Three months after making his first-team debut, in January 2007, he was sent out on loan to Belgian club Royal Antwerp, to gain match experience.
[5] In November 2007, Gray was loaned to Crewe Alexandra on a one-month deal to provide cover for the club's injured players.
[5] Gray was to enjoy his first spell of first-team football during the 2008–09 campaign, with the player signing for Championship side Plymouth Argyle on loan in January 2009 until the remainder of the season.
[11][12][13] He made his Plymouth debut in a 3–1 away defeat to Arsenal in the FA Cup two days after signing,[14] and went on to make 15 appearances in all competitions during his loan spell.
[21][22][23] Gray started the 2010–11 season as a regular in Darren Ferguson's side, making his debut in a 2–0 home loss to Doncaster Rovers on the first day of the campaign.
[30][31] As expected, he missed the first month of the new campaign as a result of his delayed start to pre-season training,[30] but eventually made his comeback appearance as a second-half substitute in a 2–1 defeat to Southampton in the League Cup on 21 September 2011.
[35] He made his debut for the club on the opening day of the 2012–13 season, playing the whole match in a 3–1 home win against AFC Wimbledon in the League Cup.
[41] At the end of the season, Gray wrote himself into Hibernian folklore by becoming the captain of the first Hibs side to win the Scottish Cup in 114 years, scoring the stoppage-time winner against Rangers in the 2016 final.
[44] Gray suffered an achilles tendon injury during a friendly game against Willem II in January 2018,[45] which meant that he did not make another first-team appearance in the 2017–18 season.
[60] He held this position for three games, including a League Cup final defeat by Celtic, until the appointment of Shaun Maloney on 20 December.
[64][65] Following that fourth stint as caretaker manager, Gray was appointed head coach on a three-year contract in June 2024.