Southend United in 2014 Bentley was born in
Basildon, Essex and began his career as a
centre back with hometown club Hutton Medway. A one-off appearance as a
goalkeeper was witnessed by an
Arsenal scout, He was released in 2008 and quickly signed for
Southend United, Bentley was sent out on
loan to
Conference South club
Braintree Town initially on cover for one match. He made his first-team debut for the Shrimpers on 22 October 2011 in a 4–1 win over
Torquay United, replacing the injured
Glenn Morris in the second half. Following an injury to first choice
Southend United goalkeeper
Paul Smith, Bentley was called upon to deputise and played in his first run of first-team matches in the 2012–13 season, making his full debut for Southend on 22 September 2012 against Exeter City, a match Southend won 2–1. Bentley went on to play further matches against
Plymouth, and
Burton Albion before Paul Smith returned to full fitness. Bentley continued to play in cup matches, and developed a reputation for being a good penalty saver. As a consequence, with a
Football League Trophy southern area semi-final against
Oxford United seemingly heading to Penalties, Southend manager
Paul Sturrock substituted starting goalkeeper Paul Smith for Bentley in the 90th minute, provoking an angry reaction from Smith. Bentley went on to save
Alfie Potter's spot kick and Southend won 5–3 on penalties, progressing to the Southern area final. Sturrock justified the decision by stating "Bentley has been fantastic at penalties all his career, and it worked, he saved one".
2013–14 season Bentley kept 19 clean sheets during the 2013–14 season. His impressive performances linked him with a move to
Leeds United with Leeds' manager
Brian McDermott watching Bentley in Southend's 3–0 win against Rochdale on Good Friday. After being linked with a move to Leeds, Bentley proclaimed that he would not let the speculation of a potential move affect his performances.
2014–15 season Over the summer of 2014 Bentley was linked with moves to Premier League clubs, but eventually remained at Southend, and in the early part of the following season he was considered for the
England U21s, however he was not selected. In the 2014–15 season, Bentley broke
Mervyn Cawston's club record of 10 consecutive home clean sheets with 12 in a row between October and April. Southend made it the play-off final at
Wembley Stadium where they played against
Wycombe Wanderers. The match was goalless after 90 minutes, however 5 minutes into extra-time Wycombe took the lead through an own goal from Bentley. A free kick from
Joe Jacobson hit the crossbar before rebounding off of the diving Bentley's back into the goal. However, with 20 seconds remaining, Southend took the match to a penalty shoot-out, in which Bentley was the hero after saving penalties from
Matt Bloomfield and
Sam Wood, meaning that Southend won promotion to
League One. The season was full of accolades for Bentley, winning all three of the club's end of season awards – supporters' player, players' player and community player of the year. He was named the
Football League Young Player of the Month for April 2015 and made the League Two
PFA Team of the Year along with teammate
Ben Coker.
2015–16 season In the 2015 summer transfer window Bentley was subject of three bids from
Queens Park Rangers, the 3rd and final offer being £1.25m which Southend chairman Ron Martin rejected. On 31 August 2015 Bentley produced a man of the match performance away at Coventry City in a 2–2, the fine display including a penalty save. Bentley remained a Southend United player when the transfer window closed on 1 September.
Brentford in 2017. On 1 July 2016, Bentley signed for
Championship club
Brentford on a four-year contract with a compensation fee of £1.1 million. The fee would rise if Bentley reaches a certain number of appearances.
Bristol City Bentley signed for
Bristol City on 28 June 2019 on a four-year contract for an undisclosed fee. During his stay at Bristol City he was appointed club captain by manager
Nigel Pearson.
Wolverhampton Wanderers Bentley signed a two-and-a-half-year contract with
Premier League club
Wolverhampton Wanderers on 25 January 2023 for an undisclosed fee. He made his debut on 13 May in a 2–0 defeat away to
Manchester United in the
2022–23 Premier League. His home debut came the following weekend in a 1–1 draw with
Everton. On 20 April 2025, Bentley kept a clean sheet at
Old Trafford after a 0–1 away win at
Manchester United. ==Career statistics==