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In February 2019, Caldwell was named president of Oakville Blue Devils FC of League1 Ontario, the third division in the Canadian soccer league system.

Caldwell became an assistant coach of the Canada men's national soccer team under John Herdman in September 2019.

He was demoted from team captain following the promotion to captain of designated player and American national team mainstay Michael Bradley. He retired in July 2015.

In May 2013, Birmingham confirmed that they would not be taking up their option to extend Caldwell's contract, and he signed for Canadian club Toronto FC of Major League Soccer on loan for the remaining few weeks of that contract. He made his debut on 18 May, in the starting eleven at home to the Columbus Crew, and was "bitterly disappointed" by the 1–0 defeat. After his contract expired with Birmingham, Caldwell signed a two-and-a-half-season contract with Toronto FC, after helping improve the team's goals-against average from 1.5 to 1.0 goals a game. Caldwell scored his first goal with Toronto on 3 July 2013 in a 3–3 home draw to Canadian rivals Montreal Impact. On 13 July 2013, Caldwell became Toronto FC's sixth team captain in the franchise's history after incumbent captain Darren O'Dea was transferred to another club.

In December 2013, readers of "Waking the Red", a Toronto news site, voted Caldwell the team's best player of the 2013 season. He was given a similar honour by the Red Patch Boys.

On 7 July 2011, Caldwell signed a two-year contract with Birmingham City, newly relegated to the Championship. He made his debut for the club on the opening day of the 2011–12 Football League Championship season, playing the whole of a 2–1 defeat at Derby County. He came close to opening the scoring in the Europa League play-off round first leg against Portuguese club Nacional, the first time that Birmingham had participated in major European competition for nearly 50 years, when his placed header struck the foot of the post. He scored his first goal for Birmingham on 14 August 2012 in a 5–1 win over Barnet in the League Cup.

On 23 August 2010, he signed a one-year deal with Wigan Athletic, again joining up with his brother Gary. He made his Wigan debut on 24 August, a day after signing, against Hartlepool United in the League Cup second round match, playing the full 90 minutes in a 3–0 victory. He made his League debut for Wigan on 16 October 2010 away against Newcastle, his former club, at St James Park in a 2–2 draw as Newcastle came from 2–0 down to gain a point. Caldwell was released when his contract expired at the end of the season.

He played twice in Scotland's qualification for the 2006 World Cup, in a 1–1 draw with Moldova at the Zimbru Stadium in Chişinău and a 3–0 away win over Slovenia at the Arena Petrol in Celje. He took part in Scotland's 2010 World Cup qualification, playing in a 4–0 defeat to Norway as Scotland finished third, behind Norway, in their qualifying group. He briefly captained Scotland when a substitution took place in a 3–0 win against the Faroe Islands on 16 November 2010. His twelfth and final full cap came against Northern Ireland in the 2011 Nations Cup.

The highlight of Caldwell's Burnley career was lifting the Football League Championship play-off trophy as captain in May 2009. He was released by Burnley at the end of his contract following the 2009–10 season.

The 2008–09 season saw Caldwell play a major role, captaining his side to promotion to the Premier League. Making 57 starts throughout the season, the Scottish international was a virtual ever-present in the Clarets back-line.

His only two goals of the campaign came at home to local rivals Preston North End in September 2008 and away at Plymouth Argyle in March 2009.

Burnley completed the signing of Caldwell from Sunderland, minutes before the transfer deadline in January 2007. He signed a three-and-a-half year deal at Turf Moor for an initial £200,000. A further £200,000 would be payable to Sunderland at a later date. He was shortly thereafter named club captain and endeared himself to the team's fans with his uncompromising tackling and commitment.

Caldwell joined Sunderland from local rivals Newcastle United in 2004. During his time at the club Caldwell was known for his whole-hearted approach to the game and the solid partnership he formed with Gary Breen. On 23 April 2005, he scored Sunderland's winning goal against Leicester City to send his team back to the Premiership.

Born in Stirling, Caldwell began his career in England with Premier League club Newcastle United, along with his younger brother Gary. He was released by Newcastle in 2004, having previously been loaned out to Blackpool, where he scored his first career goal, against Stoke City in the Football League Trophy, and Bradford City. In 2004, he joined fellow Premier League club Leeds United on loan as part of a loan swap for Michael Bridges who went in the opposite direction, Caldwell was unable to prevent Leeds being relegated to the Championship. During his loan spell he scored once in the league, against Blackburn Rovers, which helped earn Leeds a 2–1 victory. For Newcastle he made 28 league appearances and scored twice, against Bradford City in the League Cup and Middlesbrough in the league. Once released by Newcastle, he joined local rivals Sunderland.

Caldwell won twelve caps for Scotland at senior international level. He made his debut in a 1–1 draw away in Poland at the Zdzisław Krzyszkowiak Stadium on 25 April 2001 after breaking into the Newcastle United first team. His home debut came on 12 February 2003 in a 2–0 defeat to the Republic of Ireland at Hampden Park.

Steven Caldwell (born 12 September 1980) is a Scottish former footballer, coach, and executive. Playing as a defender, mostly as a centre back, Caldwell won 12 caps for the Scotland national team and has played over 300 league matches in his career, primarily in the top three tiers of English football. Since retiring from playing, he has been working as a Major League Soccer analyst for TSN in Canada.