Walsall in 2015 Benning started his career with
Walsall, progressing through the
youth system from the under-8 side. He played as a
midfielder before gaining weight and being moved to
left-back in his early teenage years. He made his
first-team debut for Walsall at the
Bescot Stadium on 6 November 2012, in a 4–1 defeat to
Scunthorpe United in
League One, coming on as a
substitute for
James Chambers. He went on to start seven games and make four substitute appearances in the
2012–13 season. He claimed another goal in a 3–2 defeat at
Stevenage the following month and ended the
2013–14 season with 15 starts and three appearances from the bench. Benning joined
League Two club
York City on 22 January 2015 on a one-month loan, with
manager Russ Wilcox looking to provide competition for the ever-present
Femi Ilesanmi. He made his debut in a 1–1
home draw with
Burton Albion two days later Having made nine appearances He made 13 starts and 11 substitute appearances for Walsall in the
2014–15 season, Benning was released in May 2015.
Mansfield Town Benning signed for League Two club
Mansfield Town on 22 May 2015. He suffered a
cruciate knee ligament injury in October 2015 and was out of action for four months; he tested his recovery from the injury by
tackling a brick wall. Manager
Adam Murray had initially worried that Benning could be ruled out for the whole of the
2015–16 season. Still, it transpired that no surgery was necessary to repair the damage as 12 weeks in a brace was sufficient to allow the body to heal itself. He signed a new contract of undisclosed length in May 2016, having scored four goals from 33 games. He signed a new one-year contract in February 2018. However, he was
sent off in a 1–0 defeat to
Accrington Stanley at
Field Mill on 31 March, a lack of discipline which caused him to be criticised by newly appointed manager
David Flitcroft. He scored a winning goal against local rivals
Chesterfield on 14 April, which earned him the nickname "Sir Mal" from supporters. Benning featured 55 times over the course of the
2018–19 season, missing just one league game. Flitcroft was sacked after the defeat, though Benning said that he was ready to focus on football again after returning from holiday in Mexico and that he and the rest of the squad had had positive meetings with new manager
John Dempster. However, the new season went poorly and Dempster was replaced by
Graham Coughlan in December. Benning played 39 games in the
2019–20 season, which saw Mansfield finish 21st on
points per game after the season was curtailed early due to the
COVID-19 pandemic in England. However, he would regain his first-team spot and earned praise for his consistency from manager
Nigel Clough in January. On 27 April 2021, it was announced that he would leave Mansfield to "seek a new challenge" with the decision made "amicably and mutually", having made 251 appearances in a six-year stay at the club. He stated that "one massive regret is to not have been able to help get the club promoted"; he was the 18th highest appearance maker in
the club's history at the time of his departure.
Port Vale in 2022 On 28 June 2021, Benning agreed a one-year contract with
Port Vale, to begin on 1 July; he was signed to compete with fellow new arrival
Dan Jones. He was dropped to the bench after
James Gibbons returned from injury, but came on as a
half-time substitute to score his first goal at
Vale Park in a 3–1 win over
Barrow on 16 October. He was limited to 17 league starts in the
2021–22 campaign, but would score the winning
penalty kick in the
penalty shoot-out victory over
Swindon Town in the
play-off semi-finals. He started in the
play-off final at
Wembley Stadium and scored Vale's final goal as they secured promotion with a 3–0 victory over former club Mansfield Town; Michael Baggaley of
The Sentinel wrote that Benning was "excellent" and he "set up
Harratt's opener, went close to scoring in the first half then confirmed Vale's victory with a sliding
volley for the third five minutes from time". He signed a new one-year contract in June 2022. He enjoyed an excellent run of form at the start of the
2022–23 season, maintaining a first-team place despite competition for the left-wing-back position from
Dan Jones,
Liam McCarron and
Thierry Small, whilst
Chris Hussey was allowed to leave the club. Speaking in December, manager
Darrell Clarke said that Benning "has defended very, very well; it hasn't been one of his main strengths but he has been good going forward, he has added that to his game and been ultra-consistent". He did though lose his first-team place to
Sammy Robinson as the club's form tailed off in the second half of the campaign. His stay with the club was automatically extended by a year after he triggered an appearance-based clause. However,
director of football David Flitcroft said that he "wouldn't get the regular game time that he would hope for and that a move away from Vale Park would be in his best interest".
Shrewsbury Town On 3 August 2023, Benning joined League One side
Shrewsbury Town on a one-year deal. He was voted as Shrewsbury's Player of the Month for January 2024. He was initially in and out of the
first XI under
Matthew Taylor before establishing himself as a regular starter under new manager
Paul Hurst. He was named as the club's Player of the Month for January 2024 and impressed Hurst with his link-up play with midfielder
Jordan Shipley. He again won the award for February and ended the
2023–24 season with 46 appearances to his name. He signed a new two-year deal in May 2024 after settling in well following a slow start at the
New Meadow. He scored his first goal in over a year in unusual circumstances when his 60-yard free-kick bounced over
Blackpool goalkeeper
Harry Tyrer on 4 December 2024. He reached his 400th career league appearance in the
2024–25 season. The campaign ended in relegation, however, as the club cycled between three managers – Paul Hurst,
Gareth Ainsworth and
Michael Appleton. He reached his 500th career appearance in professional football in February 2026. He had been frozen out of the first-team under Appleton, before returning under new manager
Gavin Cowan, who described the achievement as "
Incredible. It reflects the gentleman that he is, the professional that he is, and the player that he is". It was confirmed on 24 April, that Benning would depart the club upon the expiry of his contract at the end of the season. ==International career==