Anderton kicked off his football career in the Southampton Tyro League and had a successful time with Itchen Saints when they were doing well. His talent was evident, and he started playing for more prominent professional clubs at a young age.
Portsmouth’s manager, Alan Ball, saw his potential and allowed him an apprentice opportunity. He made a name for himself at 18 when he scored a goal against Liverpool’s youth team at Anfield. His debut for the leading squad happened in an October 1990 League Cup match against Cardiff City. He played 20 times in that season. When Jim Smith took over as the manager, Anderton became a regular player during the 1991-92 season. He even scored his first goal against Blackburn Rovers.
His performances got even better and caught the attention of bigger clubs. He scored a significant goal in a crucial match against Liverpool in the FA Cup semi-final. As a result, he moved to Tottenham Hotspur in 1992 for £1.75 million.
Tottenham and England
After a slow start, Anderton found his groove at Tottenham, playing on the right wing and being part of an exciting attacking trio with Teddy Sheringham and the young Nick Barmby. Terry Venables gave him his first chance to play for England against Denmark in 1994. Anderton became a regular player for England and turned down an offer from Manchester United in 1995 after an exciting season with players like Jürgen Klinsmann. He said he later regretted this decision candidly, but we still love you anyway, Darren.
Despite missing most of the 1995-96 season due to surgeries and injuries, Anderton played a crucial role in England’s Euro 96 team that reached the semi-finals. He was part of a team with notable players like Paul Gascoigne, Alan Shearer, Steve McManaman, and Teddy Sheringham. In the semi-final against Germany, Anderton came very close to scoring a winning goal, but his shot hit the post.
Injuries limited Anderton’s international appearances after that. He missed part of the 1997-98 season but was selected for the 1998 FIFA World Cup. He started the first two matches on the right wing, ahead of David Beckham. Coach Glenn Hoddle believed Anderton was just as good as Beckham at crossing and even better at defending. He eventually played alongside Beckham, and both players scored spectacular goals. Anderton won the League Cup with Tottenham the following year and signed a new contract.
Injuries continued to trouble him (he got given the name sicknote by the Tottenham Faithful, although Some feel this is harsh due to the number of appearances he made for the club), keeping him sidelined during Euro 2000. However, he regained fitness and played for England again, including matches against France and Italy. 2001 there were rumours of him moving to Liverpool, but he stayed loyal to Tottenham. He continued to perform well and earned a call-up to the England squad under Sven-Göran Eriksson.
Anderton’s England career had an interesting note: his last five caps were given to him by five different managers. He struggled with injuries, missing the World Cup, and despite offers from other clubs, he stayed with Tottenham. He had a positive start to the 2003/04 season but faced challenges when managers changed. His time with Tottenham ended in 2004 due to contract issues. He played 364 games for Tottenham and scored 51 goals. Despite promises, his testimonial didn’t happen.
Life After Spurs
Birmingham City made a surprise move to bring in Anderton without any transfer fee for the 2004-05 season. His standout moment with the team was when he scored the winning goal in a 1-0 triumph against Liverpool at Anfield.
Anderton’s time with Birmingham was short, and he left the club for free after just one year. He joined forces with Glenn Hoddle again, this time at Wolverhampton Wanderers, and signed a one-year contract at the beginning of the 2005-06 season. During his time with Wolves, he played in 24 matches and managed to score once in a league game against Sheffield Wednesday. He also found the net in a 5-1 victory over Chester City in the League Cup. However, his contract was not extended when the season came to an end.
On September 8, 2006, Anderton made a move to League One team AFC Bournemouth on an arrangement where he would be paid based on his playing time. He started off strong by scoring an incredible 40-yard free kick in his first match against Scunthorpe. On February 10, 2007, he achieved a milestone by scoring his first career hat-trick against Leyton Orient. Portsmouth’s manager Harry Redknapp praised Anderton after a pre-season friendly in July 2007, stating that he could still be a Premiership player with the right team and players around him.
Starting the 2007/08 season, Anderton was appointed as the new captain of the Cherries by manager Kevin Bond. He led the team’s efforts to avoid relegation, winning six out of the last seven matches. Unfortunately, a 1-1 draw with Carlisle on the final day led to Bournemouth being relegated to League Two. Earlier in the season, Bournemouth had been docked 10 points due to financial issues, which prevented them from finishing higher.
Anderton committed to another year with Bournemouth at the start of the 2008/09 season, extending his career beyond his 37th birthday. However, on December 4, 2008, he declared that he would retire on December 7, 2008, a day after his final game against Chester City. In his farewell match against Chester, Anderton made a storybook ending to his football journey, scoring a stunning volley in the 88th minute as a substitute in the second half, marking his exit from the sport.