Premier League outfit Tottenham Hotspur announced the signing of David Bentley in a £17m deal including £2m in add-ons on July 31, 2008. Spurs signed the Englishman from Blackburn Rovers.

David Bentley signed a six-year deal as a new Tottenham Hotspur signing until the summer of 2014. It was reported that Spurs’ North London rivals Arsenal were entitled to £7m due to the sell-on clause in the transfer that took him from Arsenal to Blackburn Rovers.

England international David Bentley played his first competitive game for Spurs in the 2-1 defeat to hosts Middlesbrough on August 16, 2008. His first goal for the club came in the UEFA Cup on September 18, 2008. Bentley was on target against Polish team Wisla Krakow in the first round tie of the 2008/09 UEFA Cup.

David Bentley scored his first goal for Tottenham Hotspur in the league during the North London Derby with former club Arsenal. He scored a dipping 43-yard volley as the two teams served up a classic which ended in a 4-4 draw in October 2008. His form would later dip for both club and country.

Bentley was linked with a move to Aston Villa after one year at Spurs but the player would later deny those transfer rumours

At the start of the 2009/10 season, Bentley played second fiddle to fellow Englishman Aaron Lennon on the right wing of the Spurs attack. To this effect, he was used as a substitute most times. He scored one of the goals as Spurs made history by thrashing Wigan Athletic 9-1 in a Premier League clash. Bentley scored a freekick which found the back of the net off the back of Wigan Athletic shot stopper Chris Kirkland and into the net.

English winger Bentley was sent on loan to clubs like Birmingham City and former team Blackburn Rovers while he was a Spurs player before the club decided to terminate his contract one year earlier than scheduled in June 2013.