Born in South London, despite many sources quoting his birthplace as Cambridge, which was where he moved to (Huntingdon) when a child and attended Hinchingbrooke School.
Darren was a junior athlete with a time of 10.5 seconds for 100m and was an accomplished long jumper.
As a youngster, he made rapid progress through the youth ranks at Ipswich Town, being part of the side that reached the FA Youth Cup semi-final in 2000-2001, having already signed professional and featured in the reserves. In November of that year, Darren made his Ipswich Town debut as a substitute in a UEFA Cup tie against Swedish club Helsingborg at the age of 17 and in the same month scored his first goal against Newcastle United.
At the end of the 2001-02 season, Ipswich were relegated, but they qualified for the UEFA Cup once more through the Fair Play system. In October 2002, Darren scored his first European goal against Slovan Liberec. Scoring 18 goals that season, he went into the following campaign confident and scored the only goal against West Ham United in the Division One promotion play-off final first leg, something that happened the following season too and when the Tractor Boys lost out for the second year running, the club decided to cash in on the striker and sold him to Charlton Athletic in June 2005 for anything between £2.7 million to £3.5 million (depending on the source). Darren scored twice on his debut against Sunderland to start a successful first season with the Premiership Player of the Month award, saw him finish as top scorer in his first season at the Valley with 22 goals and get voted Charlton's Player of the Year. Was runner-up to Wayne Rooney in the PFA Young Player of the Year award.
In July 2006, Bent signed a four year extension to his contract, won the Addicks' Player of the Season award again for 2005-06 and despite being injured during 2006-07, netted 15 times.
Gained England caps at Youth and Under-21 level, where he scored heavily, before finally earning a full debut against Uruguay at Anfield on 1st March 2006. Missed out on a place in the England squad for the 2006 World Cup despite being the highest English goal-scorer in the Premier League.
On relegation, there was much rumour that Darren would be bought up by one of the Premiership's big names, with Liverpool and Spurs in the running, but he turned down a move to West Ham United, who offered £70,000 a week and met Charlton's valuation of £17 million. Liverpool looked elsewhere to sign Torres and that left Spurs with the opening to sign Bent for £16.5 million on a six year deal and on wages of approximately £35,000 (so it was reported. With Ipswich's sell-on clause kicking in and a condition that if he played two back-to-back England matches, they would receive £200,000, the amount Charlton paid the Suffolk side was £2.58 million.
Struggled to adapt in his first season at Spurs and injuries did not help, but was on the bench in the League Cup Final, getting a winners medal in the 2-1 victory over Chelsea. Played the following season's final in the penalty shoot-out defeat to Manchester United, but even though he finished top scorer for the club in season 2009-10, he was constantly linked with moves away from White Hart Lane and in the summer transfer window, he eventually signed for Sunderland in a long running transfer saga. His fee was initially £10 million, but would rise to the £16.5 million Tottenham paid for him if certain criteria were met.
Spent a season and a half at the Stadium of Light and scored 32 goals in 58 games for the Black Cats, but surprisingly put in a transfer request a day before being transferred to Aston Villa for a fee that could total £24 million if certain conditions are met. Spurs were to receive 20% of the profit made by Sunderland from the sale of the forward as part of the transfer that took him away from White Hart Lane. Bent marked his Villa debut with the only goal of the match against Manchester City.