Garry was born in Bedford, and he started his career in Devon with Torquay United, where he was a trainee.
He completed his apprenticeship at Southampton and made his Premier League debut in November 1998 against Derby County.
Garry had five loan spells while at Southampton and he spent time with Torquay United, Stockport County and Oxford United before being recalled due to injuries at his parent club, and later Sheffield Wednesday and Barnsley.
Garry's first professional goal came during his loan spell at Barnsley, when he scored in a 2-1 FA Cup win against Bristol City in December 2003.
Released by Southampton in February 2004, Garry joined Barnsley permanently before making the move to Swansea City later that year.
Garry made the first of his 267 appearances for Swansea in August 2004 and he played a part in the side which won promotion from League Two in his second season with the club.
He was appointed Swansea captain in 2006 but after just two appearances, his season came to a cruel end after he suffered a knee injury.
In 2008, Garry captained Swansea to the second tier of English football for the first time in 24 years, and three years later he led the Welsh club back to the top-flight for the first time since 1983, as they beat Reading in the play-off final at Wembley.
In February 2013, Garry was introduced from the bench as Swansea won the League Cup - the club's first major trophy in English football - by beating Bradford City 5-0.
Garry stepped down as club captain at Swansea in the summer 2013, but his playing career continued, and in February 2014 he was appointed interim player manager, following the departure of Michael Laudrup.
His first game was a 3-0 South Wales win against Cardiff City and he also led the Swans into the last 32 of the Europa League. Garry also presided over Swansea's Premier League safety and he was awarded the job on a permanent basis in the summer of 2014.
In Monk's first full season as manager, Swansea finished eighth in the Premier League and racked up a record points tally.
Garry left Swansea later that year, but returned to management at Leeds United in the summer of 2016 when he became the club's sixth appointment in the space of two years.
He went on to become the longest-serving manager under Leeds owner Massimo Cellino and guided the team to a seventh placed finish in the Championship - their highest league placing since 2011.
Garry opted not to extend his stay at Elland Road beyond one season and was appointed Middlesbrough manager on June 9 2017.