Despite the fact that he had shown a large amount of promise and shone during loan spells with Norwich City and Blackburn Rovers, it became clear that David Bentley was never going to be a part of Arsene Wenger's plans at Arsenal.
And so in 2006, the Englishman dubbed 'the new David Beckham' made a permanent switch to Blackburn Rovers.
It was at Ewood Park that he started to show that maybe Wenger had been a little hasty in sanctioning his exit. In three seasons, he made 102 Premier League appearances for Rovers, scoring 13 goals - including a hat-trick in a memorable 4-3 win over Manchester United.
That form captured the attention of Tottenham Hotspur, who shelled out a reported and hefty £17m to secure the 23-year-old's services five years ago today. It was now time for Bentley to prove that he did have the ability to play for one of the division's bigger clubs.
© PA Photos
He started off well enough, scoring in a UEFA Cup tie against Wisla Krakow, before looping the ball into the Arsenal net at the Emirates Stadium from 40 yards out as a frantic North London derby ended 4-4.
During the second half of the campaign, though, injuries and the form of Aaron Lennon meant that Bentley was often forced to sit in the stands or among the substitutes.
It was a trend that he would be unable to break over the next two campaigns and as a result he was loaned out to Birmingham City in 2010. The injury problems continued at St Andrew's, as they did during other loan stints with West Ham United, Russian side FC Rostov and his former club Blackburn.
His Spurs deal expired earlier this summer and it was no surprise that after 42 Premier League outings and three goals, he was released. With the new season fast approaching, the former England international is currently without a club.
