When Gary Caldwell was appointed manager of Exeter City in October 2022 he was only the club’s third manager in sixteen years since Paul Tisdale (2006-18) and Matt Taylor (2018-22). A former Scottish international, who had most notably played for Hibernian, Celtic and Wigan, he had managed Wigan, Chesterfield and Partick Thistle by the time he arrived at St James’ Park. Remaining in post for three-and-a-half years, before returning to Wigan, City performed competently in League One during his tenure as well as enjoying runs in the FA Cup and League Cup.

Leaving school in Scotland in 1998, Gary became a trainee with Newcastle United (for whom his older brother Steven - later with Sunderland, Wigan, Burnley and Birmingham - was a professional) where he spent six years before joining Hibernian. Moving on to Celtic in 2006 and Wigan in 2010 (when he was part of the squad that won the FA Cup in 2013), he was also capped fifty-five times for Scotland.

Entering into management with Wigan in 2015, he steered the club to promotion to the Championship in 2016 ahead of spells with Chesterfield and Partick Thistle between 2017 and 2019. Later acting as under-23s manager at Newcastle and overseeing player loans at Manchester City, he also was assistant manager at Hibernian until April 2022.

Freshly available at the time of Matt Taylor’s departure to Rotherham United in October 2022, and considering that Matt had been an 'internal appointment' to succeed Paul Tisdale, Gary represented the first managerial arrival from outside the club since 2006. With the Grecians newly-promoted from League Two, Gary’s team - which he worked to remould from the outset - finished 14th at the end of his first season.

This was bettered by 13th place in 2023/24 as the squad started to show more of an emphasis on good-value loan signings from bigger clubs and slightly less-emphasis on ‘home grown’ players than in previous seasons. A notable feature of the campaign was the club's best performance in the Football League Cup for more than thirty years as the Grecians reached the 4th round (last sixteen) following a win over Premier League Luton Town at the previous stage. 

Mixed in with the arrival of more experienced players on relatively short-term contracts, the Grecians finished 16th in 2024/25 to achieve the club’s best run of three successive seasons since the 1980s. This time there was success in the FA Cup as City reached the 4th round only to lose to Nottingham Forest on penalties. 

2025/26 started against the backcloth of the sudden departure of the club's chairman along with that of the chief executive. Two further changes of chair occured in Novmeber 2025 and February 2026 at a time when the club was forced to borrow in the region of £600,000 from the supporters' trust. Although the team enjoyed good runs of form mixed in with rather more barren spells - as in the fashion throughout Gary's time as manager - performances steadied as the Grecians maintained one of the best defensive records in the division. The FA Cup threw up a run to the 3rd round and a heavy defeat at the hands of Manchester City at the Etlhad Stadium watched by nearly 8,000 Exeter supporters.     

Within weeks of that game there was immediate speculation over Gary returning to his old job at Wigan Athletic following the departure of former Plymouth Argyle manager Ryan Lowe. His re-appointment at the Lancashire club was duly announced on 16 February 2026 in the wake of City’s home game against Northampton Town which had left the Grecians in 14th place (played 30, points 39) in League One with one of the best defensive records in the division. Heading to Wigan, then 22nd in the same division, Gary Caldwell arguably left St James’ Park at a time when his popularity was at its’ highest but also when matters behind the scenes were particularly uncertain. Carefully handling the club’s trials and tribulations in front of fans and media alike, he had brought stability to City’s playing fortunes in the third tier of English football for three-and-a-half years.