Caldwell played his youth soccer in Edinburgh and soon gained recognition, with Newcastle United taking him to St James' Park at the age of 14.
The Magpies also signed his brother, Gary, at the same time. Steven signed professional terms in 1998 and made his debut in September 2000.
Although with Newcastle until 2004, Caldwell only made 37 appearances for the Tyneside club and was loaned out to several teams during his stint in the North East.
He spent time at Blackpool, Bradford City and Leeds United, but again saw little playing time.
He joined Sunderland in June 2004, penning a three-year deal. At the Stadium of Light, Caldwell got his first real taste of regular gametime, playing 76 times before leaving for Burnley in January 2007.
After three years at Turf Moor, he signed for Wigan Athletic in the summer of 2010, joining his brother at the club.
He joined Birmingham City after a year at Wigan and featured in 90 matches over two seasons before moving to MLS club Toronto FC in May 2013.
During his third year at the Canadian club, Caldwell suffered an ankle injury and announced his retirement in July 2015.
He made 12 appearances for Scotland and won the Championship title with Sunderland in 2004/05.
The early years
Caldwell was born in Stirling and got his first break in soccer when Edinburgh boys' club Hutchison Vale recruited him to their youth team.
There he caught the eye of the Newcastle scouts, who took him, aged 14, to St James' Park. His brother Gary, two years younger, was also signed and the siblings began life in the Magpies' youth teams.
He signed a professional contract in 1998 and the following year was part of the first-team squad. He did not make an appearance but was on the bench for a couple of games, giving him a sample of the matchday atmosphere.
He made his Newcastle debut on September 30, 2000 as a second-half substitute against Manchester City.
Then Newcastle boss Bobby Robson said of the youngster: "He's a steady character, has an indomitable spirit and we like him very much."
The following campaign saw Caldwell make nine league appearances and another in the League Cup, where he scored his first goal for the club against Bradford City in a 4-3 victory.
However, he did not make the expected breakthrough and began a series of loan moves to gain more experience in 2001.
Spell at Newcastle United
Despite making his debut in 2000, Caldwell struggled to secure a regular first-team berth and it seemed inevitable that he would be farmed out to other clubs.
He featured three times for Newcastle at the start of the 2001/02 season, playing in the UEFA Intertoto Cup, but then moved on loan to Blackpool.
In a month-long deal, Caldwell scored one goal in seven appearances for the Lancashire outfit before returning to Newcastle.
He was then sent out on loan to Bradford City in December 2001, with the month-long deal extended until the end of January 2002. The defender made nine appearances for the Yorkshire club.
The 2002/03 campaign was Caldwell's best for Newcastle, as he featured 17 times and scored his first and only league goal for the club. That came against Middlesbrough during his seasonal debut on November 2.
He made a brief substitute appearance against Italian club Inter Milan in the UEFA Champions League on November 27 and started the match with German side Bayer Leverkusen in February 2003.
His contract was due to expire in June 2003 and he rejected the offer of a new deal, saying: "I don't want to spend my time in the reserves." But he then made a U-turn and signed a new one-year deal on June 19.
However, gametime was, once again, hard to come by and, after just seven outings, he joined Leeds United in February 2004 in a loan swap deal involving Michael Bridges.
He secured a regular starting spot at Elland Road, making 13 Premier League appearances and scoring one goal during his spell at the club.
Career at Sunderland
Caldwell was released by Newcastle at the end of the 2003/04 campaign and made the short hop to join the Magpies' rivals Sunderland. He penned a three-year contract and got a first taste of life as a regular starting center back.
He stated that it was his intention to help the Black Cats gain promotion to the Premier League and he was as good as his word as they won the Championship title under manager Mick McCarthy.
The Scot played 41 league games during his first season, scoring four goals, while he featured in three cup games and scored another goal.
With Sunderland in the top flight, Caldwell had competition for a first-team berth and made 24 Premier League appearances, without scoring in 2005/06. He enjoyed a few runs in the side but was generally part of a rotation policy in defence.
He received a straight red card against Fulham on January 2, 2006 and was suspended for one match while also receiving another sanction for accruing five yellow cards.
The player received eight in total during the campaign, which ended in Sunderland being relegated back to the Championship as they finished bottom of the table.He captained the side on three occasions that season and was appointed skipper for 2006/07.
He started life back in the Championship having recovered from an injury but was then sidelined for three months with a knee problem. He returned in November but was unable to impress new manager Roy Keane.
In January 2008, his club accepted an offer from Burnley and Caldwell left Sunderland after 81 appearances in all competitions and having scored five goals.
Burnley years
Caldwell's move to Turf Moor was not completed until minutes before the January transfer window closed, with the defender signing a three-and-a-half-year deal.
He made his debut in a 3-1 defeat to Queens Park Rangers on February 3, 2007. He secured a starting spot in the Clarets defence and was soon appointed captain, making 17 appearances before the end of the campaign.
Injuries hampered his second season with Burnley but he still managed 29 league outings and captained the side when playing. He became a favorite with the club's fans due to an uncompromising style which resulted in eight yellow cards during the campaign.
He was sent off against Hull City on March 4, 2008 for two bookable offences, while he scored two goals that season.
The 2008/09 season was Caldwell's busiest and best in a Burnley shirt as he stayed relatively injury free to enjoy 57 outings in all competitions, scoring twice.
Captaining the side, he made 45 Championship appearances and was sent off twice as Burnley gained promotion to the Premier League via the playoffs. They beat Sheffield United 1-0 in the playoff final.
Following on from his most successful campaign at Burnley, 2009/10 was once again injury-blighted, limiting him to just 13 appearances and one goal.
He suffered two separate groin problems, the second of which forced him to miss three months of the season. He was released at the end of the campaign after 119 Burnley appearances and having scored five goals.
Spell at Wigan Athletic and Birmingham City
Caldwell was a free agent in the summer of 2010 and signed a one-year deal with Premier League Wigan Athletic. However, he found himself struggling for gametime and spent most of the season on the bench.
He managed just 10 league outings and 15 in all competitions. His brother Gary was also at the club and the siblings played together in defense on three occasions.
His spell with Wigan was not deemed a personal success and he left the DW Stadium when his contract expired in the summer of 2011.
Birmingham City manager Chris Hughton signed him on a free transfer that summer, with Caldwell penning a two-year contract.
The Blues had been relegated at the end of the previous season after finishing 18th in the standings and so he was, once again, in the Championship.
He enjoyed a successful first year at St Andrews, making 43 league appearances and six in the Europa League - Birmingham had qualified for Europe's second-tier competition by winning the League Cup.
Once again, the home fans took to the Scottish defender and he enjoyed an excellent relationship with Hughton. Injury ended his season prematurely and he missed the playoff semifinal loss to Blackpool.
He returned to the starting lineup the next season with new manager Lee Clarke at the helm and scored his first goal for the club on August 14, 2012 in a 5-1 League Cup victory over Barnet.
After being benched for a few games, Caldwell regained his place and the captaincy, to enjoy 38 outings in all competitions, scoring twice.
Illness caused him to miss the last two months of the season and he was released in the summer of 2013 after playing 90 times for the West Midlands outfit.
Move to Toronto FC
Caldwell saw out the final weeks of his Blues contract on loan at MLS club Toronto FC, making his debut on May 18, 2013 against Columbus Crew.
He then penned a two-and-a-half-year deal with the Reds and scored his first goal in a 3-3 draw with Columbus on July 3.
The player was soon appointed captain and proved very popular with the Canadian club's supporters, who voted him best player of the 2013 campaign.
He made 23 appearances in his first season and 21 the following year as Toronto finished seventh in the standings to miss out on the playoffs.
The 2014 MLS season was frustrating for Caldwell as he suffered with injury, while also being sent off against Sporting Kansas City on May 24.
He missed a month with a quad tear in July and then went down with another injury on his return to sit out several more weeks.
He returned in September and played out the rest of the campaign, stating that he was now focused on the next season.
However, having played two early games for Toronto in 2015, Caldwell suffered Achilles tendon problems in mid March and was on the sidelines for a month.
He did not play another match, announcing his retirement on July 14 after 49 games for the club.
It was a disappointing end to what had been an enjoyable spell in North America.
International career with Scotland
Caldwell made his debut for the Scotland Under-21 side in a 2-0 loss to France in March 2000. He then played alongside brother Gary against Belgium and went on to make 10 appearances for the Under-21s.
He got the call to join up with the Scotland B side and played three times, scoring his only goal against Turkey on December 10, 2003.
In April 2001, while at Newcastle, he made his senior debut in a 1-1 draw with Poland. He made his home debut on February 12, 2003 in a 2-0 defeat to the Republic of Ireland.
On May 30, 2004, Caldwell replaced his brother in the 79th minute of a 4-1 win over Trinidad and Tobago but he made only sporadic appearances until his final cap against Northern Ireland in the 2011 Nations Cup.
He did appear in defense next to his brother on a few occasions but his senior international career was a disappointment, with only 12 caps and no goals.
Personal life
Caldwell grew up in the town of Stirling, 37 miles from Edinburgh and admitted that Scotland and Liverpool legend Kenny Dalglish was his hero as a child.
He is married to Angela and the couple have two children, Will and Robbie. He took his family to Canada when joining Toronto and they remained there after the end of his playing days.
He enjoys a close relationship with brother Gary and stated that he was glad the pair did not have to face each other domestically during their playing days.
It nearly happened when Steven was at Burnley and Gary played for Wigan but an injury to Steven prevented the siblings from doing battle.
He moved into the media in 2015, working as a commentator and studio analyst for MLS games with Canadian network TSN.
In February 2019, he was named president of Oakville Blue Devils FC who play in the third tier of the Canadian soccer league.
In September 2019, Caldwell was given an opportunity to return to the game when appointed assistant coach of the Canada men's national team. He works under English coach John Herdman, a former development coach at Sunderland's youth academy.
Caldwell continues to work in TV and combines the job with his duties as Canada's assistant coach, with his family now settled in the country.