Following his appointment as Chesterfield manager earlier this week, we take a look at Gary's career to date.
Born in Stirling, Scotland, Caldwell played at the Celtic Boys club before moving south of the boarder to sign for Newcastle United.
A centre half by trade, Caldwell would progress from the youth level to the reserve team at St James’ Park, working under coaches such as Sir Bobby Robson and John Carver. And despite not making a senior appearance with the Magpies, he would gain first team experience in loan spells with Darlington, Hibernian, Coventry City and Derby County.
It was during his time on loan with Hibs that he made his international debut for Scotland, unfortunately it was not one to remember as Berti Vogts’ team were beaten 5-0 by the then world champions France in Paris.
In 2004, he joined Hibernian permanently on a free transfer, appearing in the Scottish League Cup final defeat to Livingston on March, 14. Caldwell would go on to make 19 appearances in total that season, scoring one goal in a 3-0 win over Kilmarnock at Easter Road.
In May of that year Caldwell scored his first goal for Scotland, as they beat Trinidad and Tobago 4-1 at his home ground of Easter Road.
He would spend another two seasons with Hibs before joining Celtic in the summer of 2006.
Caldwell’s spell at Celtic was a very successful one, picking up a league winners medals in each of his first two seasons with the Hoops. While also collecting a Scottish Cup medal in 2007, and a Scottish League Cup winners medal in 2009.
Individual success also came at the end of the 2008/09 season as he picked up both the Scottish Football Writers Association Award and the Clydesdale Bank Player of the Season Award.
Things were also going well internationally with Caldwell establishing himself in the national team, and scoring a famous winner against France in Euro 2008 qualifier at Hampden Park. Caldwell would go on to play 55 times for his country.
Caldwell moved back to England in 2010, this time signing for Wigan Athletic in the Premier League. Marking his debut with a clean sheet in a 2-0 victory over Wolverhampton Wanderers.
He was made club captain of the Latics in the 2010/11 season and was voted the club’s player of the year.
While in 2013 he was a non-playing substitute as Wigan won the FA Cup for the first time in their history, beating Manchester City 1-0, and along with team mate Emerson Boyce jointly lifted the famous trophy.
Caldwell would remain at the DW Stadium until his retirement from playing in February 2015. And after initially spending time working with the club’s academy, he was appointed manager in April.
Despite suffering relegation from the Championship, Caldwell remained in charge for the 2015/16 season and what a season it was.
He guided Wigan back to the Championship at the first attempt, winning League One by two points from Burton Albion. His team were also the top scorers in the division, scoring 82 goals from their 46 games.
More individual success followed as Caldwell was named LMA Manager of the Year for League One, before his departure from the club in October 2016.