A talented, but controversial winger who made the move to Spurs after starting his career at Arsenal, David Bentley was a confident player, who has the ability to create things out of nothing.

As a youngster, he had the pick of Tottenham and Arsenal, who were both chasing his services.  He plumped for the Highbury club, but despite signing as a professional in 2001, he had to wait until 2003 for his debut and until May 2004 until he first featured in the Premier League.

Sent out to Norwich City to get first team experience, Bentley played in their first season back in the Premiership, but he could not help them stay up and they returned to the Championship and he returned to Arsenal in the close season.  He wasn't there for long, as he was loaned out again, this time to Blackburn Rovers for the 2005-06 season, but in January 2006, he signed permanently for the Ewood Park club for an undisclosed fee.  He became a favourite at Rovers, with his good delivery into the forwards Benni McCarthy and then Roque Santa Cruz that saw the team achieve qualification for the UEFA Cup.  In February 2006 he further enhanced his career with a hat-trick against Manchester United to help the side win 4-3.

Having been involved with the England Under-21 set-up since his debut in 2004, Bentley became the first English player to score at the new Wembley on March 2006, when he hit the net against Italy U21 in a 3-3 draw.  He signed an extension to his contract in February 2007, putting his name to a deal which would keep him at Blackburn until 2011, but his reputation was growing and in May of that year, he was called up for an England B cap against Albania, when he took the plaudits as man of the match for the side that contained Ledley King and Jermaine Jenas.  His display was followed by a call-up for the full squad's matches against Brazil and Estonia, but David did not feature in the squad.  The Under-21s had qualified for the European Championships that summer and despite being picked to travel to Holland for the finals, Bentley pulled out, saying he was too fatigued to play any more games following a hard season.  His choice not to represent his country back-fired on him, with new England manager Steve McClaren omitting him from his squad for the first friendly of the season as a punishment and then when he did get his full debut at home to Israel, he was booed by the fans for wanting to represent his country.

In between, he continued to star for Blackburn and help them progress in the UEFA Cup, but in April 2008, Bentley revealed a gambling habit, which saw him making multiple bets each day and his girlfriend helped him deal with the issue by getting him interested in do-it-yourself, otherwise he would have been in a downward spiral of addiction.

With Blackburn Rovers manager Mark Hughes adamant that he did not have to sell Bentley, rumours about interest in the winger began ahead of the summer transfer window and when Hughes move don to take over at Manchester City, David made it known that he too wanted to move clubs.  With Tottenham coming in with offers shortly after the season had ended, they were initially knocked back by Rovers, as Aston Villa also tried to tempt Bentley away from Ewood Park.  In the end, it was at the end of July when Bentley signed for a fee that could reach £15 million. 

His early form under the management of Juande Ramos failed to impress, as he was played out of position (even at left back) and his criticism of the Spanish coach came just before Tottenham sacked Ramos in an attempt to halt their poor form at the start of the season that left Spurs with two points from eight games.  With Harry Redknapp taking over as manager, Bentley's form improved and he scored a stunning volley from thirty yards out in the 4-4 draw at Arsenal. 

Had a troubled remained of the season, as Harry Redknapp could not understand why the club had spent big money on a right winger, when Aaron Lennon was already playing right wing.  Bents knuckled down and trained well, without criticising the manager and had the courage to step up at Wembley to take a penalty in the League Cup Final shoot-out, although his effort missed the target.

Ended the season out of the side and picked up a dead leg in pre-season that kept him out of much of the build-up to the 2009-2010 campaign.  Looked fit against Olympiakos, but then crashed his car in Potters Bar, Hertfordshire when drunk at the wheel of his Porsche in the week before the season started.  His performances were limited to the odd substitute appearance and then a few games towards the end of the season when he came in to relieve Aaron Lennon and he didn't do too badly. 

However, a poor showing in the League Cup tie against Arsenal at the start of the 2010-11 campaign saw the crowd get on his back and he went out on loan to Birmingham City in the January transfer window for the remainder of the season to get some first team game time.  It was not a hugely successful move, as he was not a regular in the side, suffered injury, walked out of the ground after being left out for a game at Wolves and Birmingham ended up getting relegated in the last minute of the last game of the season ... at Tottenham; a game Bentley could not play in for either side because of the Premier League loan rules.