Early Career
Following a trial, he was selected to play for the Thurrock District squad at Herringham Primary School in Chadwell St. Mary. He was invited for a trial by Arsenal after being spotted playing for Thurrock in a tournament when he was just seven years old. There was also interest from other teams, such as Millwall, West Ham United, and Tottenham Hotspur.
When he began training with Arsenal at the age of eight, he wasn’t right away a top player for the team. He was one of three players from the group who wouldn’t be traveling to Spain. He also became one of the team’s top players later on, captaining the young teams, and at the age of 16, he was awarded a two-year scholarship.
During the first year of his scholarship, he sustained a knee injury that kept him out of action for four months.[4] He learned from Arsenal in the spring of 2018 that they would not offer him a professional contract once his scholarship ended.
Burnley
After learning of his availability, Burnley of the Premier League extended an invitation for a trial. Also, after a brief trial, the club’s under-23 manager, Michael Duff, persuaded him to sign in the summer of 2018. After being provided with a clear path to the first team, he agreed to a two-year professional contract.
A few months later, Steve Stone succeeded Duff as manager of Cheltenham Town after Duff left to take the position. The two men got along well in spite of this. Benson regularly started training with the first team and was included in the squad for a January 2019 away game against Manchester United at Old Trafford, however he was not used as a substitute.
During Burnley’s journey to Portugal for their preseason games for the 2019–20 season, he had a huge impact. After preseason, he expected to be a fixture on the first-team squad, but an injury hampered his progress. Despite this, Josh remained a mainstay on the under-23 team and occasionally held the position of captain.
Additionally, he signed a loan agreement with EFL League Two outfit Grimsby Town on January 18, 2020, where he collaborated with fellow under-23 player Anthony Glennon to obtain first-team experience. Manager Ian Holloway’s prior scouting work at Blackpool with Burnley’s chief operating officer Matt Williams led to the deal.
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Williams offered Glennon when Grimsby was in severe need of a left-back, and Benson followed a week later after Holloway had seen him play a few times. He made his professional debut in February 2020, scoring the game-winning goal in the 86th minute to help his team defeat Morecambe 2-1.
He was only on loan for two months since the COVID-19 pandemic ended the season early, but he made a good impression on Holloway by scoring twice in 11 matches. After the Premier League started in July, Benson sat on Burnley’s bench for a few games, but he didn’t participate in any of them.
In the summer of 2020, Burnley initiated a one-year contract extension on his arrangement. In August 2020, Holloway called Burnley and asked them to lend Benson and Glennon back to Grimsby.
Because of the tiny size of the squad and the lack of transfer activity, Burnley decided to keep him on staff despite receiving bids from EFL Championship sides for him to go out on loan once more.
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On September 17, 2020, he made his first team debut against Sheffield United in an EFL Cup game. He replaced Ashley Westwood as the Clarets advanced on penalties. The next week, during Burnley’s 2-0 victory over Millwall at The Den, he made his entire debut in that same competition.
On November 28, 2020, when Burnley headed to Manchester City at the City of Manchester Stadium, he took Josh Brownhill’s position in the starting lineup due to injury. Despite the team losing 5-0, Sean Dyche called his performance “terrific” and noted that he played the entire 90 minutes.
A few days after the game, Steve Stone alleged that plans had been made to loan him out during the January transfer window. He got a new contract in December 2020 that extended until June 2023 with an additional 12-month extension in the club’s favor after making five first-team appearances.
