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Bertrand has been described as a modern-day full-back who gives assistance in attacking down the flanks, keeping and retaining possession as well as defending and reclaiming possession, making quick runs into the box and often does one-two's with his teammates. Bertrand was described by Glenn Roeder, his manager at Norwich, as a defender who "likes to bomb forward and is tenacious in the tackle when defending." In a 2018 ESPN FC article about the state of left-backs in England, Michael Cox said that the "only real star is Ryan Bertrand, a truly excellent full-back defensively and offensively".

Bertrand was part of the squad for UEFA Euro 2016. On 1 September 2017, Bertrand scored his first goal for England in a 4–0 World Cup qualifier win over Malta.

Bertrand scored his only goal of the 2015–16 season in the final match, a penalty in a 4–1 win over Crystal Palace. On 12 July 2016, Bertrand signed a new five-year contract.

On 2 February 2015, Bertrand completed a permanent move to Southampton, signing a 4½-year deal for an undisclosed fee, estimated to be £10 million. On 26 April, he was the only Southampton player named in the PFA Team of the Year.

Bertrand came on as a substitute for England away to Italy on 3 March 2015 and he won his fourth full cap, starting for England against Republic of Ireland in Dublin on 7 June 2015.

On 17 January 2014, Bertrand joined Aston Villa on loan for the remainder of the 2013–14 season. He made his debut the next day in a 2–2 draw with Liverpool.

On 30 July 2014, Bertrand joined Southampton on loan for the 2014–15 season. He made his competitive debut for the club on 17 August in their first match of the league season, playing the full 90 minutes of a 2–1 defeat away to Liverpool. Bertrand scored for Southampton the first time on 27 September, opening a 2–1 home win against Queens Park Rangers. His second goal for the club came on 26 December, in a 3–1 victory over Crystal Palace. On 1 February 2015, he was given a straight red card at the end of a 0–1 home loss against Swansea City for a foul on Modou Barrow.

He was used as a back-up to Cole by Chelsea manager Carlo Ancelotti, as he remained with Chelsea and left back Patrick van Aanholt went out on loan. Six years after signing for Chelsea as a schoolboy, Bertrand made his first starting appearance, against Fulham in the League Cup. The match finished in favour of Chelsea, who won on penalties 4–3, as the match ended goalless.

On 1 April 2013, he came on as a replacement for Ashley Cole in the FA Cup quarter-final replay against Manchester United, which Chelsea went on to win 1–0. It was revealed after the match that Cole would be sidelined for at least two weeks, leaving Bertrand as the clubs only recognised left back. He started the next match, the Europa League quarter-final first leg against Rubin Kazan at Stamford Bridge, putting in a strong performance as Chelsea ran out 3–1 winners. On 7 April, Bertrand made his 50th Chelsea appearance in a 2–1 win against Sunderland.

He started at left back in the FA Cup semi-final against Manchester City at Wembley Stadium on 14 April, which ended in a 2–1 defeat for Chelsea. In the continued absence of Ashley Cole, Bertrand started and performed well in the next league match in the West London derby against Fulham at Craven Cottage on 17 April, which Chelsea comfortably won 3–0 thanks to a 30-yard strike from David Luiz and a brace from John Terry.

Bertrand is an England international, having also represented 'the Young Lions' at under-17, under-18, under-19, under-20, under-21 levels, as well as Great Britain at the 2012 Summer Olympics. On 15 August 2012, he made his debut for the England senior team, in a friendly against Italy, in a 2–1 win.

Bertrand made his European debut in the 2012 UEFA Champions League Final against Bayern Munich on 19 May 2012, playing on the left of midfield, becoming the first player in the Champions League era to make his debut in the final. He was substituted with a knock after 70 minutes and replaced by Florent Malouda as Chelsea edged out Bayern 4–3 on penalties.

Bertrand scored his first professional goal for Chelsea in the Community Shield match against Manchester City on 12 August 2012, which they went on to lose 3–2. He started in the first league match of the season against Wigan Athletic playing as a winger. On 5 September 2012, Bertrand signed a new improved five-year contract with Chelsea. On 25 September, he scored his second professional goal in a League Cup match against Wolverhampton Wanderers at Stamford Bridge, which Chelsea won 6–0.

On 2 July 2012, Bertrand was named in Stuart Pearce's 18-man squad for the 2012 Summer Olympics. He played his first match for Great Britain on 20 July 2012 in a friendly match against Brazil. He played three matches during the Olympic tournament.

On 10 August 2012, Bertrand was called up to the senior England team for the first time, for a friendly match against Italy. He made his international debut coming on for Leighton Baines in the 78th minute and cleared a shot off the line minutes later from Manolo Gabbiadini which eventually led to England's winning goal as England won the match 2–1.

On 11 September 2012, Bertrand came on after 73 minutes in the 2014 FIFA World Cup qualification match against Ukraine and crossed the ball that led to the penalty that Frank Lampard converted. On 8 October 2012, Bertrand was called up to the England squad for two more qualifying matches, against San Marino and Poland. However he missed both matches because of a virus.

Born in Southwark, London, Bertrand began his youth career at Gillingham, before signing for Chelsea in July 2005. He graduated from Chelsea's youth system and was sent on loan to various clubs between 2006 and 2010. He made his full debut for Chelsea on 20 April 2011, six years after joining them, in a fixture against Birmingham City. In the 2011–12 season, Bertrand signed a new four-year contract with Chelsea and was made understudy to Ashley Cole, whom he described a "fantastic role model." On 19 May 2012, Bertrand became the first player to make his Champions League debut in the final, starting in an unfamiliar left wing role in front of Cole; Chelsea beat Bayern Munich 4–3 on penalties. He has honours with Chelsea, including an FA Cup, UEFA Europa League and UEFA Champions League titles.

Bertrand made his Premier League debut on 20 April 2011, when he came on as substitute to replace Ashley Cole in a 3–1 win against Birmingham City. Bertrand also made a goal, providing a cross which Florent Malouda headed past Birmingham goalkeeper Ben Foster.

On 15 July 2011, Bertrand signed a new four-year contract with Chelsea.

During the 2011–12 season, Bertrand played 90 minutes in Chelsea's 2–0 defeat against Liverpool in the League Cup. He made his first league appearance of the season coming on as a late substitute for Ashley Cole against Everton, the match ended in a 2–0 defeat for Chelsea. Bertrand was handed his first Premier League start against Wigan Athletic on 7 April, in which he produced an outstanding performance, as Chelsea won 2–1 and he was named fan's man of the match. He was again named man of the match in his third start, a 0–0 draw with Arsenal on 21 April. On 5 May, Bertrand won the FA Cup with Chelsea, but he did not appear on the pitch in the win against Liverpool.

On 5 August 2010, Bertrand signed on loan with Championship club Nottingham Forest in an initial six-month deal. He made his debut for Forest as a substitute in a 1–0 away defeat against Burnley. He was a regular for Forest for whom he made a total of 19 appearances. Forest were interested in either extending Bertrand's loan spell for the rest of the season or to sign him permanently but when his loan period expired on 3 January 2011 he returned to his parent club Chelsea.

On 17 July 2009, Bertrand joined Reading on a season-long loan. He scored his first professional goal against Derby County on 10 March 2010. He came third in the voting for Reading's player of the season, behind Gylfi Sigurðsson and Jimmy Kébé.

He was promoted to the U21s and called up for several 2009 European Championship qualifiers, but missed out of the squad for the final tournament. On 14 November, Stuart Pearce selected him at left back for an under-21 match against Portugal at Wembley in Group 9 of the qualification process, and helped the team keep first clean sheet since 29 June 2009. He was named in the England under-21 squad for the 2011 European Championship and played all matches.

On 4 January 2008, a matter of days after his spell at Oldham came to an end, Bertrand joined Norwich City on loan for the rest of the 2007–08 season. He put in a number of impressive displays playing at both left full back and on the left wing, and admitted he would welcome a longer stay with the club. Bertrand became popular with the Carrow Road crowd earning him the nickname 'Plastic' in reference to the Belgian singer Plastic Bertrand. On 4 July 2008, he rejoined the club on loan until January 2009, with an option to extend to the end of the season.

He was part of the U19 squad at the 2008 European Championship.

In August 2007, Bertrand joined Oldham Athletic on loan until January 2008.

During the 2006–07 season, he was twice sent on loan to AFC Bournemouth, at the same time as Chelsea teammate Jack Cork. He suffered a ruptured spleen in a youth team match against Arsenal that ruled him out of the later part of that season.

Bertrand was signed by Chelsea in July 2005 from Gillingham for an initial £125,000, which was set by a tribunal and is subject to increase depending on progress.

Ryan Dominic Bertrand (born 5 August 1989) is an English professional footballer who plays as a left back for Premier League club Southampton and the England national team.