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On 15 January 2019, Caulker joined Alanyaspor of the Turkish Süper Lig. Caulker was on board the minibus that crashed in Alanya, 29 April 2019. Josef Šural was killed in the accident. Caulker and several teammates were driven to a nearby hospital, with non-life-threatening injuries from the crash.

Caulker started the first six Alanyaspor games of the 2019–20 season after which his team were unbeaten and top of the league. Alanyaspor lost their next game 2–0 at Beşiktaş in which Caulker was an unused substitute.

6 weeks after departing QPR, on 8 February 2018 Caulker signed a one-and-a-half-year deal with Dundee. He scored on his debut for Dundee in a 3–2 loss at Kilmarnock on 13 February 2018. In April 2018, Dundee rejected a club-record bid for Caulker from Norwegian champions Rosenborg. In the late hours of the transfer window on 31 August, Caulker left Dundee, after he triggered a clause in his contract.

In 2017, Caulker spoke at length about the issues that had plagued his personal life since he began his professional career and the steps he had undertaken to overcome them.

In June 2017, Caulker was interviewed by The Guardian and discussed his problems with alcohol, gambling addiction and depression. Caulker acknowledged that his problems had damaged his football career and had led him to consider suicide.

Caulker's loan with Southampton was cancelled on 12 January 2016 to allow him to join fellow Premier League club Liverpool on loan until the end of the season. Caulker made his Liverpool debut on 13 January 2016 in the 3–3 draw with Arsenal at Anfield when he replaced Adam Lallana as an auxiliary striker in the 87th minute. For the next two league matches, home against Manchester United and away against Norwich City, he entered the match as striker in the 90th minute, contributing to the 95th-minute winner by Lallana in the latter.

On 29 July 2015, Caulker joined Premier League club Southampton on a season-long loan. He made his debut for Southampton in the second-leg of their Europa League third qualifying round match against Vitesse Arnhem, on 6 August 2015. Caulker only made eight appearances for Southampton, the last of which came in a 6–1 home defeat by Liverpool on 2 December 2015.

On 22 July 2014, Caulker transferred to Queens Park Rangers for an undisclosed fee, signing a four-year contract. He scored his first goal for the club in a 2–2 home draw against Stoke City on 20 September. He turned down an offer to join his former Swansea City manager, Brendan Rodgers, at Celtic in the summer of 2017, later stating "[Joining Celtic] came close. I decided in the end to stay in London. I was early on in my recovery, and I felt my support network was best in London." Caulker left Queens Park Rangers by mutual consent on 28 December 2017.

He was sold to newly promoted Cardiff City for the 2013–14 season but was unable to prevent their relegation from the Premier League. He was subsequently sold to Queens Park Rangers for the following 2014–15 season; who themselves were relegated. He spent the next few seasons largely on loan to Southampton and Liverpool before playing half a season for Dundee in the Scottish Premiership. He then joined Turkish Süper Lig team Alanyaspor in January 2019.

On 31 July 2013, newly promoted Premier League club Cardiff City signed Caulker from Tottenham for a club record fee in excess of £8 million, on a four-year contract. Caulker made his Cardiff debut in their first league match of the season a 2–0 defeat against West Ham United, on 17 August 2013. Caulker scored his second league goal for Cardiff in a 1–0 home win against former loan club and rivals Swansea City, the winning goal in the first ever South Wales derby in the Premier League. On 8 March 2014, he scored twice in a 3–1 win against Fulham. Caulker was ever-present for Cardiff in the Premier League playing every minute of the campaign scoring five goals, but was unable to prevent them from suffering relegation back to the Championship.

Caulker was named along with fellow Spurs loanee Ryan Mason in the England U19s for three European Championship qualification matches in Slovenia, appearing in matches against Finland and Slovenia. Caulker achieved his third and fourth caps for the U19s in friendlies against Turkey and the Netherlands respectively. Caulker was again included in the England U19 squad for the Elite Round of qualification in the Ukraine for the European Championships. Caulker played the full 90 minutes of England U19's first two matches, beating Ireland and Bosnia and Herzegovina 1–0 and 4–0 respectively. Caulker also played the full 90 minutes in the final match against Ukraine, a 1–1 draw enough to take England through to the European Championships by winning Group 3 of the Elite qualification round. Caulker was again called up for the final 18-man squad for the European Championships, for group matches against Austria, the hosts France and the Netherlands. Caulker started all three group matches, a 3–2 win over Austria, a 1–0 defeat to the Netherlands and a 1–1 draw with France confirming England's progress to the semi-final stage. England reached the semi-finals, where Caulker earned his 11th cap as England lost 3–1 to Spain. Caulker had started all of England's matches and played all bar a couple of minutes of their games in the tournament. Due to being overage for the next European Championships, Caulker along with the majority of the previous England U19s was not included in the squad for the friendly against Slovakia in September 2010.

In November 2013, then Scotland assistant manager Mark McGhee confirmed interest in Caulker, as Caulker's grandmother, Jessie, comes from Dollar, Clackmannanshire. Since his only full England cap was in a friendly, he is permitted to change allegiances. In March 2018 Caulker declared his desire to play for Scotland. His then manager at Dundee, Neil McCann, said, "I would love him to pull on the dark blue for Scotland." In October 2019 Caulker contacted then Scotland Assistant Manager, Steven Reid, to express his desire to play for Scotland.

On 5 July 2012, Caulker signed a new four-year contract with Tottenham Hotspur until the summer of 2016. Having been an unused substitute at the start of the season, on 20 September 2012, Caulker made his European debut in the UEFA Europa League group stage match against Lazio, helping his team keep a clean sheet in a 0–0 draw and having a goal harshly disallowed. The following weekend, Caulker made his Premier League debut for Tottenham Hotspur as a half-time substitute in the 2–1 home victory over Queens Park Rangers. Caulker retained his place and received his first Tottenham league start in the next match against Manchester United, with Tottenham eventually winning the match 3–2, breaking a 23-year winless run at Old Trafford. After the match, centre back partner William Gallas praised Caulker for his performance and felt in time he would become one of the best defenders in England. On 7 October 2012, Caulker scored his first goal for Tottenham in their 2–0 home win against Aston Villa, redirecting a Jermain Defoe shot into the back of the net in the 58th minute of the match. He scored his second goal for the club on 11 November 2012, opening the scoring with a header in a 2–1 defeat away to Manchester City. Caulker finished the season having made 28 appearances in all competitions for Tottenham, scoring two goals.

On 2 July 2012, Caulker was confirmed in Stuart Pearce's 18-man Great Britain Olympic football team squad for the 2012 Summer Olympics, and Caulker made his Team GB debut in the pre-Olympic friendly 2–0 defeat against Brazil. Caulker started all three of Great Britain's group stage matches, including a clean sheet against Uruguay, as the GB team qualified for the knockout stage of the Olympic tournament. Caulker finished the Olympics having received five caps for Team GB, as they were knocked out in the quarterfinals on penalties to South Korea. On 10 August 2012, as part of a new look national team squad Caulker was called up to the senior England team for the first time, ahead of a friendly match against Italy, although he failed to make it onto the pitch.

On 31 August 2012, Caulker was called up to the England U21 squad for the European U21 Championship qualification matches against Azerbaijan and Norway. On 6 September 2012, Caulker scored his second consecutive England U21 goal in the team's 2–0 win over Azerbaijan to ensure qualification to the U21 qualification play-offs. Caulker played the full 90 minutes in both of England's play-off matches against Serbia with England's 2–0 aggregate victory marred by ugly scenes after the final whistle. The mass brawl and accusations of racial abuse, later led to the Serbian police charging 11 people in relation to the mass brawl including Caulker and Leeds United player Tom Lees. On 13 December 2012, Caulker was handed a two-match ban by UEFA due to the incident, although in February 2013 this ban was rescinded and instead Caulker was ordered to do a day of community service. Caulker was included in the England U21 squad for the 2013 UEFA European Under-21 Championship, and played in the first two of England's group matches as the team lost all three of their matches and failed to progress to the semi-finals.

On 8 November 2012, Caulker received his second call up from Roy Hodgson to the England national football team for the friendly against Sweden. Caulker started the friendly against Sweden on 14 November and scored a debut goal when he turned in a Steven Gerrard free kick from the right from three yards out. He played the first 74 minutes before being substituted with England leading 2–1. The team eventually lost 4–2.

Just five days after his Tottenham debut, Caulker was loaned out to Championship club Bristol City until the end of the season where he joined Spurs teammate Danny Rose. He made his Bristol City debut in the 3–1 away defeat to Portsmouth. In his 50th professional match, on 16 October, Caulker scored his first goal in Bristol City's 3–2 defeat against Cardiff City. Thanks to his outstanding form helping guide Bristol City away from the relegation zone, Caulker was rewarded with Young Player of the Month for the npower Football League for November. Caulker scored his second goal of the season with an injury time equaliser in the 2–2 draw with Queens Park Rangers, on 3 January 2011. On 28 March 2011 his season was cut short due to a knee cartilage injury which ruled him out for the rest of the 2010–11 season and so returned to Tottenham for treatment and surgery on his ankle. His 30-match loan spell received praise from both manager Keith Millen and former England goalkeeper David James, described in his Observer column as 'quality' and one of Bristol City's 'best players'. Caulker won Bristol City's Young Player of the Year award for the 2010–11 season and was a nominee for Player of the Year.

In early June 2011, Caulker was linked to a further season-long loan move to help continue his development through regular football, this time to newly promoted Premier League clubs Swansea City and Norwich City, as well as another stint at Bristol City. On 1 July 2011, Caulker officially joined Swansea City on a season-long loan, with Swansea paying an initial fee for his services and an option to review the loan in January. Former member of Spurs' backroom staff and Newport County manager Anthony Hudson described Caulker as having the "potential to be one of the best defenders in country". Hudson said during his time at Bristol City, Caulker was "the best defender in the Championship" and described him as "one to watch this season because I think he's going to be a real star". He made his Premier League and Swansea City debut in the 4–0 away defeat to Manchester City, playing the full 90 minutes. After featuring in all of Swansea's first four Premier League and keeping two clean sheets, Caulker suffered a knee cartilage injury when he collided with a goalpost in Swansea's match against Arsenal. The injury ruled him out for around eight weeks. Despite initially targeting his return for the match against Manchester United on 19 November 2011, Caulker returned to action after three months out in the 2–0 home victory over Fulham on 10 December 2011. Caulker became a mainstay for the remainder of Swansea's Premier League campaign and made 26 starts overall, helping the club finish 11th in the Premier League.

On 5 November 2011, Caulker was arrested for a public order offence after an incident in Swansea city centre. He was issued with a fixed penalty notice and later released. Caulker later revealed that his arrest was for swearing in the street and apologised to the club and his manager Brendan Rodgers for getting caught-up in the late night offence.

After returning from the U19 European Championships and a successful loan spell Caulker was awarded with a new contract until 2013. In early August a Daily Mirror report suggested Caulker may again be loaned out, this time to Championship club Leeds United, in a bid to continue his development through regular competitive football, but this deal fell through when Caulker sustained a groin injury. He made his Tottenham debut in a 4–1 home defeat, after extra time, against Arsenal in the Carling Cup on 21 September 2010.

Caulker received his first call-up to the England U21 squad for the friendly against Germany on 16 November 2010. He made his debut in that match, coming on as a 77th-minute substitute for Martin Kelly in a 2–0 defeat. In February 2011 Caulker was called up to the England U20 squad for their friendly against France but withdrew after an injury. Caulker was named in the 31-man U21s squad for two warm-up matches for the 2011 U21 European Championship with friendlies against Denmark and Iceland but had to pull out through injury and missed both matches, and the treatment of this injury caused Caulker to miss out on a call-up to the 40-man provisional squad for the 2011 European Championship. Caulker was recalled to the U21s team for the double-header matches against Azerbaijan and Israel in September 2011 and featured in both matches. On 13 January 2012, Caulker was named on Stuart Pearce's shortlist for the 2012 Summer Olympics Great Britain Olympic football team. Having been watched by Fabio Capello during Swansea's 3–2 victory over Arsenal, Caulker was tipped for a call-up to the England squad for their friendly against the Netherlands, in an attempt to tie his future down to England due to his eligibility for Scotland. On 23 February 2012, Caulker was called up for England U21's 2013 European Championship qualification match against Belgium. Caulker started and scored his first international goal in a 4–0 victory on 29 February 2012.

Caulker started his professional career with Tottenham Hotspur in 2009. He spent three seasons on loan with Yeovil Town, Bristol City and Swansea City. At Swansea he made his first appearances in the Premier League and at the end of the season played for Britain at the 2012 Olympics. In November 2012 he made a scoring England debut in a friendly against Sweden.

In July 2009, Caulker went on loan to League One club Yeovil Town along with teammate Ryan Mason. He made his league debut at the start of the 2009–10 season against Tranmere Rovers, where Yeovil won 2–0. After impressing in Yeovil's 0–0 draw with Oldham, Caulker made the Football League Team of the Week. Along with fellow Tottenham loanees Ryan Mason and Jonathan Obika, on 5 November 2009, his loan was extended until the end of the 2009–10 season. On 1 March 2010, Caulker was included in the Team of the Week for a second time following the 1–0 home win against MK Dons. Caulker returned to Spurs one match early after starting 44 of Yeovil's 45 league matches, having missed only one match due to playing for England U19s, also taking four of Yeovil's five end of season awards. In November 2013, he was selected to be part of Yeovil Town's 'Team of the Decade', which was voted for by the club's fans to commemorate their tenth season as a Football League club. Caulker was the only loan player to be chosen.

Despite being a talented athlete as a teenager, Caulker chose to pursue a career in football, playing his early football with Hounslow Borough, his local club. After initially playing as a central midfielder, he acted on advice from a coach and made the switch to central defence. After a single match at centre back for Hounslow at the age of 15, he was offered trials with seven clubs including Tottenham Hotspur, Chelsea, Reading and Queens Park Rangers. Caulker joined the Tottenham Hotspur youth team and having broken into the Under-18s team as an Under-16 player during the 2007–08 season Caulker progressed to make 31 appearances and scored one goal in 2008–09. He also forced his way into the reserve team that season, making five appearances, and captained the Under-18s towards the start of that season. He impressed during his first season as a full-time scholar and signed his first professional contract at Tottenham in July 2009.

Steven Roy Caulker (born 29 December 1991) is an English professional footballer who plays as a centre back for Alanyaspor. He has made one appearance for the England national team and represented the Great Britain Olympic football team at the 2012 Summer Olympics.