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In June 2019, Bennett proposed to Cherie in Ibiza. Since then they are expecting their third child together, due 2020.

Ahead of the 2018–19 season, Cardiff signed fellow left-back Greg Cunningham from Preston North End to provide competition for Bennett. He described Cunningham's arrival as "motivation" to him, with the pair sharing the role in the opening months of the campaign. Three days prior to a match against Arsenal in January 2019, Bennett's father suddenly died. Electing to play in the match, Bennett played the full 90 minutes in a match described as "emotionally charged" in the first fixture since the disappearance of Cardiff's new signing Emiliano Sala in a plane crash. He finished the campaign having made 30 appearances in the Premier League as Cardiff suffered relegation to the Championship.

With Cardiff, he gained promotion to the Premier League after finishing as runners-up in the Championship during the 2017–18 season. At international level, he has been capped at U-19, U-20 and U-21 levels for England.

During the summer of 2017, fellow Championship side Fulham met a release clause in Bennett's contract. However, he rejected the move to stay in the Welsh capital, with manager Neil Warnock confirming that Fulham's offer contained a significant wage increase. His first goal of the season came at Reading on 11 December. He was sent off following two yellow cards in an FA Cup match against Manchester City on 28 January. Bennett later issued a public apology for the first bookable tackle on Leroy Sané, which left the opposition player injured, following backlash from fans on social media and pundits. Former referee Mark Halsey described the foul as a "potential leg-breaking tackle." Cardiff manager Neil Warnock made Bennett train alone after the incident as punishment and was left out of the first team following the arrival of loan signing Armand Traoré but was eventually restored to the side by Warnock. During the 2017–18 season, Bennett helped the club win promotion to the Premier League after finishing as runners-up in the Championship, making 40 appearances in all competitions. At the end of the season, he was handed a new three-year contract with the club.

He then joined Sheffield Wednesday on 19 January 2016 for the rest of the season. He made his debut against Shrewsbury Town on 30 January, where Wednesday were knocked out of the FA Cup in a 3–2 defeat. He went on to make four appearances as Wednesday made the play-offs, losing in the final against Hull City. On his return to Villa, Bennett was informed by manager Roberto Di Matteo that he was not part of his first team plans, leading Bennett to enter into talks over a permanent move over to Hillsborough. The move was later blocked by new Villa owner, Tony Xia, which he insisted was for financial reasons, with Xia believed to be unhappy over the terms of the deal which included subsidising Bennett's wages, and to avoid selling a player to a divisional rival.

On 27 August 2016, Bennett joined fellow Championship side Cardiff City on a free transfer. After suffering a calf injury, Bennett was forced to wait two months before making his debut in a 2–1 Severnside derby victory against Bristol City on 14 October. His first goal for Cardiff came on 18 March 2017, in a 3–1 win over Ipswich Town and he concluded the season, with a brace against Huddersfield Town on the final day.

Bennett began the 2015–16 season with Villa, scoring his first goal for the club in a 5–3 victory against Notts County in the League Cup on 25 August 2015. Despite initially hoping to return to the first team under new manager Tim Sherwood, he was loaned to newly promoted A.F.C. Bournemouth on an initial six-month loan deal on the final day of the summer transfer window, signing a one-year contract extension with Villa prior to his departure. Signed as cover following injuries sustained by Tyrone Mings and Charlie Daniels, Bennett was described by manager Eddie Howe as possessing "everything the modern day left-back needs." However, he failed to make an appearance for the side and suffered an achilles injury after a month resulting in his return to Villa in January 2016.

Bennett and his fiancé Cherie have two sons together, Jesse-Oliver; born 4 September 2015 and Jaxon; born 28th September 2017.

In his second season, Bennett struggled to break into the first team, with increased competition from Luna and new signing Ryan Bertrand and persistent injury problems, missing three months with a persistent back problem and later suffering from tendinitis in his knee. He made two appearances in the League Cup in the opening months of the season but did not make another appearance for Villa until 8 February 2014, when he replaced Bertrand during a 2–0 defeat to West Ham United. Three days later, he made his first league start of the season, playing in an unfamiliar left midfield role during a 0–0 draw with Cardiff City. He made just seven appearances in all competitions during the season.

Having lost his place in the first team to Aly Cissokho, on 21 August 2014, Bennett joined Championship side Brighton & Hove Albion on a season-long loan, with Brighton manager Sami Hyypiä describing him as "a dynamic left-back who's very comfortable on the ball." He made his debut for the club in a 2–1 victory over Bolton Wanderers on 23 August 2014. Following his arrival, Bennett described how he was "loving playing" under Hyypiä's attacking style of play and revealed that he had removed himself from social network site Twitter having been subject to abuse from Aston Villa fans. In January 2015, Bennett stated that he was open to signing for the club on a permanent basis. Bennett made 42 appearances in all competitions for Brighton, featuring in more matches than any other player at the club, before returning to Villa at the end of the season.

On 29 August 2012, after making 92 appearances for Middlesbrough in four years, Bennett completed a transfer to Premier League club Aston Villa for a fee of £3  million, with potential add-ons rising to £4.25  million. He made his debut on 22 September 2012, coming on as a substitute for Eric Lichaj during a 4–1 defeat against Southampton. In his first season, Bennett made 30 appearances in all competitions for Villa and received praise from manager Paul Lambert as the club suffered a difficult season, finishing 15th. Lambert praised Bennett for not hiding but stated his belief that the club needed to sign a player to "put pressure" on Bennett to improve, eventually adding Antonio Luna from Spanish side Sevilla to the squad.

Strachan left Middlesbrough by mutual consent after a year and the arrival of Tony Mowbray saw Bennett become a regular in the first team, as the new manager sought Bennett to play as a more attacking full-back. A proposed loan move to Bristol City was cancelled by Mowbray and Bennett was restored to the first team. He signed a new four and a half-year deal in January 2011, extending his stay until June 2015, and made 28 consecutive starts under the new manager, the longest run of any player, until he was forced to miss several games after contracting mumps. At the end of the season, Bennett won the club's Young Player of the Year award. He credited Mowbray with his improved form, commenting "without him I wouldn't be where I am now."

Bennett received his first call up for the England under-21 side after a series of impressive first team performances for Middlesbrough on 2 February 2011. He went into the squad for the game against Italy U21s, making his debut in the match as England suffered a 1–0 defeat. In May 2011, he was named in England's provisional 40-man squad for the 2011 UEFA European Under-21 Championship but was omitted from the final selection. He won his third and final cap for the under-21 side in a 4–1 victory over Israel in September 2011.

Following his spell in the reserves, Bennett secured a two-year professional deal and named in the senior squad for the first time. He was named on the bench for a number of Premier League fixtures, before making his first team debut on 24 May 2009 during a 2–1 defeat to West Ham United in the final game of the 2008–09 season, replacing Tony McMahon after 46 minutes. The defeat resulted in Middlesbrough's relegation from the Premier League.

Having been promoted to the first team, Bennett made his first appearance of the 2009–10 season in an away loss at Nottingham Forest in the League Cup, coming on as a substitute in extra time. He made his first professional start in a 2–2 draw away at Coventry City on 26 September 2009. He started Middlesbrough's three following matches, earning praise from manager Gareth Southgate. However, Southgate was sacked a month later and replaced by Gordon Strachan. During Strachan's era as manager at Middlesbrough, Bennett admitted to feeling down after struggling to break into the first team. He asked to leave the club on loan but his request was turned down, although he was later unsuccessfully offered to several clubs for between £150,000 to £250,000.

Bennett was part of the England under-19 squad at the 2009 European Championships in Ukraine in the summer of 2009. After featuring as a substitute in England's opening two group matches, draws with Switzerland and hosts Ukraine, Bennett was named in the starting lineup for his side's final group match, a 7–1 victory over Slovenia. He remained in the starting lineup for England's semifinal victory over France and their defeat to Ukraine in the final. He was due to participate in the 2009 FIFA U-20 World Cup but did not because of club commitments.

Joseph Bennett (born 28 March 1990) is an English professional footballer who plays as a defender for Championship club Cardiff City. Born in Rochdale, Bennett signed his first professional contract with Middlesbrough prior to the 2008–09 season and made his professional debut in May 2009 in the club's final game of the season. He went on to make more than 90 appearances in all competitions for Middlesbrough before joining Aston Villa on 29 August 2012 for an undisclosed fee. After one season as a regular in the first team, he struggled to establish himself in the side and, after loan spells with Brighton & Hove Albion, A.F.C. Bournemouth and Sheffield Wednesday, he was sold to Cardiff City in 2016.