Ryan Bertrand was born in south London on 5th August 1989 but started his football career in Kent, joining Gillingham at the age of nine.
The Premier League came calling in 2005 when, shortly before his 16th birthday, Bertrand was snapped up by Chelsea for a fee of £125,000.
Among his fellow scholars at his new club was future Saint Jack Cork, and the pair’s respective careers would go on to be closely intertwined.
On Friday 3rd November 2006, having turned professional at the start of the campaign, the duo joined League 1 side AFC Bournemouth on loan in time to make their debuts that very evening, starting in a 4-2 defeat to Swansea City.
Bertrand and Cork played together in all-but-one of the left-back’s seven appearances for the Cherries, which were spread across his two loan spells at Dean Court that season before his campaign was curtailed by an injury.
Ryan began the 2007/08 campaign out on loan once again, returning to League 1 with Oldham Athletic. After 22 appearances for the Latics, he moved up a division to join Norwich City in January.
It was with the Canaries that Bertrand would play at St Mary’s for the first time, helping his loan side to a 1-0 win there in January 2008.
He returned to Carrow Road the following season, but would end the campaign disappointed as the side was relegated to League 1 – a fate also suffered by Southampton.
Bertrand joined his fourth loan club in July 2009, linking up with his old Chelsea youth boss Brendan Rodgers at Championship side Reading.
Rodgers left the club in December, but Bertrand stuck around for the whole campaign, racking up 51 appearances and scoring his first professional goal in a 4-1 win over Derby in March 2010.
His next loan destination was Nottingham Forest, where he spent the first half of the season before heading back to Stamford Bridge in January.
Bertrand was included in Chelsea’s matchday squad for an FA Cup fifth-round replay against Everton the following month, but was an unused substitute.
Ryan made his long-awaited first-team debut for Chelsea on 20th April 2011, coming on as a second-half substitute for Ashley Cole with the side 2-0 up against Birmingham at Stamford Bridge. Within five minutes, he had set up Florent Malouda to score the third goal in a 3-1 win.
That would be his only first-team appearance for the Blues that season, though he did make the bench a further two times.
In the summer of 2011, Bertrand – along with Chelsea teammate Cork – was named in the England squad for the UEFA European Under-21 Championship finals. He started all three of the Young Lions’ games as they exited at the group stage.
Bertrand made his first start for Chelsea in September 2011, playing the entirety of a Carling Cup win over rivals Fulham that was settled by penalties.
He continued to make appearances for the Blues, mostly in the domestic cups, and started a Barclays Premier League match for the first time in April 2012 as he played the full 90 minutes of a 2-1 home win over Wigan Athletic.
Bertrand played a major part in Chelsea’s successful FA Cup campaign that season, appearing in the third, fifth and sixth rounds.
The high point of his campaign – and, perhaps, his career to date – came on Saturday 19th May. Having never even made a European squad for Chelsea, he was named in the starting XI for the 2012 UEFA Champions League final.
Then 22 years old, Bertrand played the first 73 minutes as Chelsea beat Bayern Munich on penalties after drawing 1-1 in the German side’s own stadium, becoming European champions for the first and only time in their 109-year history.
Another proud moment would come later that summer when the defender was named in Stuart Pearce’s squad for the 2012 Olympic Games. He was joined in the squad by pal Cork, who had departed for Southampton at the start of that season.
Bertrand made his debut for Team GB in a friendly against Brazil, and started three of their four matches during the subsequent tournament.
Barely a month later, five days after his 23rd birthday, Ryan was called into the senior England squad for the first time, making his international debut as a 78th-minute substitute in a 2-1 win over Italy in Switzerland.
Bertrand kicked off the domestic season by scoring his first goal for Chelsea, netting within nine minutes of coming on in their 3-2 Community Shield loss to Premier League champions Manchester City at Wembley Stadium.
He was promoted to the Blues’ starting XI for their league opener against Wigan Athletic and kept his place in Roy Hodgson’s squad for England’s first two 2014 FIFA World Cup qualifiers, coming on to help the Three Lions salvage a point against Ukraine at Wembley Stadium after being an unused substitute against Moldova days earlier.
The 2012/13 campaign would see him play for Chelsea 38 times as they won the UEFA Europa League and reached the semi-finals of the FA Cup and Capital One Cup.
However, the following season would prove less fruitful for the full-back. He played for Chelsea just three times, only one of which was in the Premier League, before moving on loan to Aston Villa in January.
He made 16 appearances for Villa before returning to Stamford Bridge in the summer to consider his future, eventually leading him to join Southampton for the coming campaign.