Bentley started his career with Arsenal in the Premier League, and despite being earmarked as one for the future, saw his playing opportunities limited by a strong senior squad.

He spent time on loan with Birmingham City, West Ham United, FC Rostov and a brief return to Blackburn before being released by Tottenham in 2013.

[1] By January 2003, he was handed his first-team debut, coming on as a substitute for Kolo Touré in the 77th minute of a 2–0 FA Cup third round win over Oxford United.

[6] Bentley's first and only goal for Arsenal was a chip shot from the edge of the penalty area over goalkeeper Mark Schwarzer, in a 4–1 FA Cup win over Middlesbrough on 24 January 2004.

[10] He returned to the team in April 2005, coming off the bench against Manchester United and playing a key role in Norwich's 2–0 win.

[14] Desiring a permanent move, Bentley was linked with a number of clubs including Wolverhampton Wanderers,[citation needed] before returning on a further season's loan, to Blackburn Rovers on 31 August 2005.

[16] Bentley went on to feature regularly for Blackburn in the 2005–06 season, and helped the club finish sixth in league standings and qualify for the 2006–07 UEFA Cup.

[18][19] In Europe, a 25-yard volley against Salzburg in the UEFA Cup helped secure Rovers' passage into the group stage,[20] where he also scored a last minute winner against Wisła Kraków.

[22][23] Commenting on the new deal, Rovers manager Mark Hughes described Bentley as "a great talent with a big future" while chairman John Williams added that he "is widely regarded as one of the best young footballers in the country.

[citation needed] Not long after the departure of manager Mark Hughes to Manchester City, Bentley reiterated his desire to leave.

[29] Bentley's form would suffer at Tottenham, however, and after falling down the pecking order for both club and country, it was reported on 17 June 2009 that he was in talks to move to Aston Villa.

[40] Despite featuring prominently in Tottenham's pre-season under new manager André Villas-Boas, on 7 September 2012, Bentley went out on loan to Russian club FC Rostov.

[46] In January 2013, Bentley's former manager at Tottenham, Harry Redknapp, attempted to sign him on loan for Queens Park Rangers as a potential supplier of crosses for Peter Crouch.

[50] On 3 August 2013, Levski Sofia manager Slaviša Jokanović expressed interest in signing Bentley and his former Tottenham teammate Cristian Ceballos.

He stated in an interview that he had fallen out of love with football, calling the modern game "robotic" due to the influence of social media and money, as well as "predictable and a bit too calculated".

[63] The next day, he was named in McClaren's 26-man full England squad for the friendly match against Brazil and the UEFA Euro 2008 qualifier against Estonia.

[64] This withdrawal led to Bentley being excluded from the senior England squad for the friendly against Germany,[65] but he was selected for the UEFA Euro 2008 qualifiers against Israel and Russia.

He made his senior debut when he came on as a substitute for Shaun Wright-Phillips against Israel, but was jeered by some of the fans due to his previous refusal to play for the under-21 team.