John Terry: Defining moments of former Chelsea captain's career

John Terry lifted the Premier League trophy five times with Chelsea

October 1998. A close-cropped teenager by the name of John Terry steps onto the pitch for the first time as a Chelsea player.

Twenty years later and five months after his final appearance, the 37-year-old has announced his retirement.

Here, we look back at the moments that defined the career of the former Chelsea and England captain.

The breakthrough

After making his debut for Chelsea in a League Cup tie against Aston Villa in 1998, it was in an unlikely setting where Terry really first caught the eye.

Towards the end of the 1999-2000 season, he went on loan for six games to Nottingham Forest, who were managed at the time by ex-England midfielder David Platt.

Former England and Tottenham midfielder Jermaine Jenas recalls his time as a youth player at Forest, when he first came across a young Terry.

"I always used to go and watch all the Forest games. Platty brought him in for Forest so our careers overlapped and we used to watch each other play in each other's positions.

"His skill is the one thing that stood out then. People talk about JT and how he was a die-hard, which is spot on - he was all-round the best centre-half I have seen in the Premier League. But one of the big things I don't think he ever got enough credit for, which I was most impressed by when I watched him as a teenager playing for Forest, is how good he was with the ball at his feet."

• Analysis: Terry was leader and legend but also divisive

A first brush with controversy

High-profile court cases made Terry a fixture on the front pages

In September 2001, Terry was one of four Chelsea players fined by the club following a drinking binge in a hotel packed with American tourists grieving over the terror attacks on New York City's twin towers at the World Trade Center.

The incident happened 24 hours after the attacks and the drunken behaviour took place at a hotel near Heathrow Airport, which was packed with American citizens stranded by flight cancellations.

The group included Terry, Frank Lampard, Jody Morris and Frank Sinclair. Chelsea's Uefa Cup game that night against Levski Sofia had been called off as a mark of respect to the victims of the 9/11 attacks.

Chelsea's then managing director, Colin Hutchinson, condemned the behaviour as "totally out of order" and said they had each been fined two weeks' wages.

Terry 'had that something extra'

In 2005, Terry became the first defender - and the first Chelsea player - to be named the Professional Footballers' Association Player of the Year.

He was recognised after helping the Blues to just their second top-flight title, while his part in Chelsea's run to the Champions League semi-finals saw him named the Uefa club defender of the year. He would go on to receive that recognition again in 2008 and 2009.

Former Fulham and England midfielder Danny Murphy played alongside Terry at international level.

"He is two-footed and has always been a good footballer and a good reader of the game because that is a gift," said Murphy. "But straight away he always had that tenacity he became known for and a willingness to put his body on the line - that old-fashioned centre-half mentality.

"That whole combination made him an obvious candidate to become an international footballer and as the years went on he got more confident and became even better.

"There have been some other really good centre-halves but even if it is only marginal, he is ahead of Rio Ferdinand, Ledley King and Jamie Carragher. They were all top players but JT just had that something extra that made him the top one for me."

A turbulent time as England captain

Terry made his first appearance as England captain against Greece in August 2006

Terry's England career brought him 78 caps and periods of heavy turbulence, including an episode that led directly to the departure of coach Fabio Capello.

He made his debut in June 2003 against Serbia and Montenegro and started the 3-1 win against Croatia at Portman Road on 20 August that year.

Terry played for England at Euro 2004 in Portugal and the World Cup in Germany two years later, England going out to the Portuguese on penalties in the quarter-finals on both occasions. He succeeded David Beckham as England captain shortly after the 2006 World Cup.

In January 2010, an injunction stopping the media reporting on Terry's alleged relationship with Vanessa Perroncel, the former partner of his ex-Chelsea and England colleague Wayne Bridge, was lifted by the High Court, and the episode was to have major consequences for Terry's England future.

Terry hit the headlines again after falling out with former Chelsea team-mate and friend Wayne Bridge

He was stripped of the captaincy by then coach Capello in February of that year.

Terry figured in the ill-fated World Cup in South Africa, where England lost 4-1 to Germany in the last 16, but was reinstated as captain in March 2011 as Rio Ferdinand struggled with long-term injury.

He was removed from the role by the Football Association in February the following year while he was waiting to stand trial over racial abuse allegations following an incident involving Anton Ferdinand at QPR during a Premier League game in October 2011.

England coach Capello challenged the FA's decision and resigned within days after talks failed to resolve the differences.

An FA statement read: "The discussions focused on the FA board's decision to remove the England team captaincy from John Terry and Fabio Capello's response through an Italian broadcast interview.

"In a meeting for over an hour, Fabio's resignation was accepted."

Terry was cleared at Westminster Magistrates' Court of abusing Ferdinand in July 2012 but he retired from England duty in September 2012 saying his position had become "untenable" because the FA pursued a charge of racially abusing Ferdinand during the game at Loftus Road.

He was subsequently found guilty, banned for four matches and fined £220,000 by the FA. A spokesman for Terry said he was "disappointed" the FA had reached a "different conclusion" to the "not guilty verdict of a court of law".

That Champions League final penalty miss

Terry said in 2015 that he still woke up in the night thinking about the Champions League final penalty miss

Wednesday, 21 May 2008 should have been a perfect moment for Terry.

The Chelsea icon had the chance to score the penalty kick which would make his beloved Blues champions of Europe for the first time. Against their Premier League rivals Manchester United no less.

"I walked forward to take it knowing that it was there to be won and it was all down to me. What happened next will haunt me for the rest of my life," he said a week later.

The England defender slipped as he made contact and his shot cannoned off the post. United went on to win the shootout 6-5 in sudden death.

"I am so sorry for missing the penalty and denying the fans, my team-mates, family and friends the chance to be European champions," Terry said after the game

Captain at the double in 2010

Terry's first two league titles under Jose Mourinho have often been seen as workmanlike, but the third in the double-winning season of 2009-10 was anything but.

The title was clinched with an 8-0 thumping of Wigan on the final day, meaning Chelsea ended the season on 103 league goals. Carlo Ancelotti's side were the first team since Tottenham in 1961 to score three figures in the top flight.

Terry was once again integral, playing in 37 of the 38 league games and making more than 50 appearances in total.

He only managed two league goals but both were vital. The first was the only goal in a 1-0 victory over Manchester United, who finished as runners-up. And the other was a late winner in a 2-1 success against Burnley.

It helped Chelsea to become just the seventh club to claim the league and FA Cup double.

That Champions League 'celebration'

Cherlsea have reached two Champions League finals during Terry's career

Chelsea's captain lifting the Champions League trophy on the greatest night in the club's history. What's wrong with that?

Well Terry had played no part in the 2012 final - he had to watch from the stands after being sent off in the semi-final victory over Barcelona.

But after Chelsea beat Bayern Munich on penalties in the Allianz Arena, he quickly got changed into full kit to lift the European Cup.

He was lampooned on social media and became the victim of many a meme.

"Doing a John Terry" has become a popular phrase, with Leicester's Robert Huth tweeting to say he was "Going full John Terry today!!" to lift the Premier League trophy in May 2016, despite serving a three-match ban.

In May 2013 Terry was at it again, picking up the Europa League trophy as Chelsea beat Benfica, despite missing the final with an ankle injury.

The 700 club

Terry is one of only three Blues players to have played more than 700 times for Chelsea (Ron Harris and Peter Bonetti being the others).

Terry made his full debut aged 17 and just two days before he turned 21, he captained the first team for the first time - in a defeat by Charlton.

Despite a low-key ending to his Blues career, he is the most successful captain in Chelsea's history and won every major honour during his time at Stamford Bridge.

From out of favour to first on the teamsheet

Terry had a bit of a stop-start final three years to his Blues career.

An integral cog in the side that won the league under Jose Mourinho in 2014-15, he became only the second outfield player to feature in every minute of every Premier League game in a season.

Also named in the PFA Team of the Year, it was quite the contrast to his perceived worth under Rafael Benitez a year earlier.

The Spaniard, interim boss at Stamford Bridge from November 2012 until May 2013, said Terry could not play more than two games in a week and in that season he made just 14 league appearances.

His revival during Mourinho's second spell at Chelsea played a major role in the club's 2014-15 title triumph.

26 minutes for the number 26

Terry has been linked with the Aston Villa manager's job

Terry announced towards the end of the 2016-17 season that he would leave Chelsea that summer, having rarely featured in Antonio Conte's plans as the Italian guided the club to another league title.

Terry went out in typically high-profile fashion, leaving the Stamford Bridge pitch to a guard of honour after 26 minutes of his final match for the Blues, against Sunderland.

The significance of the timing? Terry was synonymous with the number 26, having worn it on his shirt during his Chelsea career.

"I kind of negotiated with the manager to play 26 minutes and come off," Terry said.

He would go on to join Aston Villa in the summer of 2017, helping them reach the Championship play-off final.

But his playing career would end in defeat by Fulham at Wembley, a ground on which he had celebrated so many victories over the years with club and country.

A version of this article was first published on 17 April 2017.