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The same day, Reilly signed for another League One club, AFC Wimbledon. He scored his first goal for Wimbledon in an EFL Trophy tie against Leyton Orient on 8 October 2019.

Reilly was a regular in the starting eleven throughout his loan spell, and on 3 July 2018 made the move permanent, signing a two-year contract. He was released by mutual consent on 26 July 2019.

Reilly joined League One club Coventry City on 1 January 2017 on loan until the end of the season, as part of a deal in which Stuart Beavon signed permanently for Coventry and Marvin Sordell moved in the opposite direction. He played regularly, making 20 appearances in all competitions and helping Coventry reach the 2017 EFL Trophy Final, but was unable to take part because of a hamstring injury suffered the previous day. Reilly was released by Burton when his contract expired.

Ahead of the 2017–18 season, Reilly signed a two-year deal with another League One club, Bury, where he was reunited with manager Lee Clark, who had given him his league debut for Birmingham. He was in the starting eleven for the opening fixture of the 2017–18 season, a 1–0 win at home to Walsall, and made 15 league starts in the first half of the campaign, after which he was loaned to League One club Gillingham.

Eight minutes into his first match of the 2014–15 season, away at league leaders Norwich City, Reilly scored the opening goal, a deflected effort from hit with his weaker right foot from 25 yards (23 m), and in the next match, he made his 50th appearance. But in the face of competition from new signings Stephen Gleeson and David Davis, and later from loanee Robert Tesche, he was unable to establish himself in the starting eleven. On 11 March 2015, he joined League Two club Burton Albion on loan until the end of the season. Birmingham manager Gary Rowett intended the loan spell as an opportunity for the player to earn a new contract. Reilly made his Burton debut as a late substitute in a 3–0 win against Accrington Stanley. He started the next match, but suffered a hamstring injury after 11 minutes that was expected to keep him out for a month and returned to Birmingham for treatment. He was released by Birmingham when his contract expired, and according to the Birmingham Mail's season summary, could consider himself unlucky.

On 5 June 2015, Reilly agreed a two-year contract with Burton Albion, newly promoted to League One, subject to passing a medical. He scored his first goal for the club against Bury in an EFL Cup tie on 10 August 2016.

With Hayden Mullins suspended and Jonathan Spector injured for the visit of Crystal Palace on 15 December, Reilly made his first start, and first appearance in the Football League, alongside Papa Bouba Diop in central midfield. He played the full 90 minutes as Birmingham came back from 2–0 down to draw. On his sixth Championship start, a 1–1 draw away to Huddersfield Town, Reilly "swept in" a knock-back from Chris Burke's cross in first-half stoppage time to score his first senior goal. He was substituted at half-time due to illness. In April, the club took up their option to extend Reilly's contract for another year. He ended the season with 18 league appearances, and signed a new two-year contract ahead of the 2013–14 campaign.

Reilly had hoped to be a regular in the first team in the 2013–14 season, but an influx of new players, including midfielders Andy Shinnie and Tom Adeyemi, meant it took until late September and a good performance in the League Cup victory over Premier League club Swansea City that he made his first league start, against Reading. In the following game, a 4–0 win against Millwall, manager Lee Clark described the performance of Reilly and Adeyemi in partnership in defensive midfield as brilliant. They played regularly together until January, when new arrivals, including Manchester City's Emyr Huws and the experienced Brian Howard, caused Reilly to fall out of favour. By the end of March, with Birmingham struggling, Reilly returned to the team, playing either in midfield or at left back. On the last day of the season, needing at least a draw at Bolton Wanderers and for other results to go in their favour to avoid relegation to League One, he started at left back, later moving into central midfield to replace the injured Huws, as the team came back from 2–0 down to equalise in the third minute of stoppage time and maintain their second-tier status.

Reilly received his first call-up to the Republic of Ireland under-21 team for a friendly match against the Netherlands on 6 February 2013. He was selected in the starting eleven, and played 64 minutes before being substituted, as Ireland won 3–0. On his second appearance, he played the first half of a 2–1 home defeat to Portugal in March. He had a chance of scoring on his first competitive appearance for the under-21s, in a European championship qualifier away to the Faroe Islands, but his shot was well saved; Ireland won 4–1.

A midfielder who has also played at full back, Reilly began his career as a youngster with Birmingham City. He made his first-team debut in January 2012, turned professional later that year, and over the next three seasons made 66 appearances in all competitions. He had a short spell on loan at Burton Albion in 2015, and joined the club on a two-year contract in June of that year. Unable to establish himself in their first team, he spent the second half of the 2016–17 season on loan to Coventry City, and then joined Bury. After a loan spell at Gillingham, he signed for them ahead of the 2018–19 season. He was released ahead of the 2019–20 season and joined AFC Wimbledon.

He was given a first-team squad number in January 2012, and his first competitive involvement came when he was named among the substitutes for the third-round FA Cup-tie against Wolverhampton Wanderers, remaining unused. Reilly made his first-team debut on 28 January, coming on as an 80th-minute substitute for Jordon Mutch in the fourth-round FA Cup-tie against Sheffield United at Bramall Lane, with Birmingham already 4–0 ahead.

He signed his first professional contract, of one year, before the 2012–13 season, and was given a squad number before the visit to Millwall in October.

Reilly was born in Warrington, Cheshire, and raised in Solihull, West Midlands, where he attended St Peter's Catholic School. He joined Birmingham City's youth system at the age of seven, and began a two-year scholarship in July 2010.

Callum Anthony Reilly (born 3 October 1993) is a professional footballer who plays for League One club AFC Wimbledon.