Career
Barrow
On 17 May 2016, Bennett signed a two-year contract at National League club Barrow.[11] It was reported that he opted to go to Holker Street ahead of competition from League Two clubs.[12] He went on to score 22 goals in 53 games as Paul Cox's "Bluebirds" finished the 2016–17 season in seventh-position, just missing out on the play-offs.
Carlisle United
On 25 July 2017, 26-year-old Bennett signed for Football League side Carlisle United for an undisclosed fee (later reported to be £50,000)[13] on a two-year contract.[14] Bennett stated that "I think I'm ready for the step up... I've still got a lot to prove, a lot to learn but I'm more than willing to get my head down and do it."[15] On 30 September, he was one of three players sent off in a 1–0 defeat at Crawley Town; he was shown a straight red card for elbowing defender Josh Yorwerth.[16] It took him 15 games before he scored for the "Cumbrians", but credited the support of his teammates and manager Keith Curle in helping him to break his scoring duck.[17] His first goal for the club came on 28 October, in a 2–2 draw at Chesterfield.[18] On 4 November, he scored a brace in a 3–2 FA Cup victory over former club Oldham.[19] He ended the 2017–18 season with eight goals in 47 appearances.
Having been limited to 13 league starts by new manager John Sheridan, Bennett signed for Morecambe on loan for the rest of the 2018–19 season on 17 January 2019; "Shrimps" boss Jim Bentley admitted he had been monitoring the player for some years.[20][21] David Holdsworth, director of football at the "Blues", said that Carlisle would monitor his progress and still retained the option of extending his contract at Brunton Park in the summer.[13] He scored five goals in 16 games at the Globe Arena, however, was not retained at the end of the season by new Carlisle manager Steven Pressley.[22]
Port Vale
On 21 June 2019, Bennett signed a two-year contract with League Two side Port Vale.[23][24] Manager John Askey said that he hoped having Bennett available to him would take pressure off star striker Tom Pope.[25] He scored his first goal for the "Valiants" on 17 August, three minutes after coming on for Pope in a 1–1 draw at Salford City.[26] Three days later he was given his first start for the club and this time scored after four minutes in what ended as a 2–1 victory over Forest Green Rovers at Vale Park.[27] He lost his first-team spot in late-November to Pope and then Mark Cullen, before scoring a brace in a 3–1 home win over Exeter City on 28 January in what was his second league start in two months; despite this achievement Bennett admitted that "it probably wasn't my best performance. I have a lot to improve, I know that myself".[28] He left the club mid-way through the 2019–20 season after scoring seven goals from 30 games.[29]
Stockport County
On 12 March 2020, Bennett signed a two-and-a-half-year contract with Stockport County after being sold for an undisclosed fee, who were just outside the National League play-offs under former Northwich manager Jim Gannon.[30] He found himself out of the team after Simon Rusk replaced Gannon as the manager in January 2021.[31]
On 1 April 2021, Bennett signed on loan for National League rivals Hartlepool United until the end of the 2020–21 season.[32] Bennett made his debut the following day as a substitute in a 2–1 win against Dagenham & Redbridge.[33] Bennett scored his first goal for Hartlepool in the following match as a substitute in a 2–2 draw at Boreham Wood.[34] Bennett earned a start for the next match against Notts County and scored his second goal for Hartlepool in a 2–0 win.[35] The following week, Bennett scored a hat-trick in a 7–2 victory at Wealdstone.[36] He was recalled to Stockport on 28 April.[37] He played for Stockport against Hartlepool in the play-off semi-finals and had a late header saved in a 1–0 defeat at Edgeley Park.[38] Hartlepool went on to win the play-off final and Bennett had his contract with Stockport cancelled in June.[39][40]
Return to Barrow
On 27 June 2022, Bennett returned to Barrow – now in League Two and managed by Pete Wild – on a two-year contract after being signed for an undisclosed fee.[47] However, he picked up an injury during pre-season. He was sidelined until November.[48] Bennett left Barrow by mutual consent on 31 July 2023.[49]
Scunthorpe United
On 2 March 2023, Bennett joined National League club Scunthorpe United on loan until the end of the 2022–23 season.[50] Scunthorpe had recently underwent a takeover and signed eleven new players.[51] He scored one goal in nine games, his sole goal coming in a 2–0 win over Altrincham at Glanford Park, as Scunthorpe were relegated to the National League North.[2][52]
On 4 September 2023, Bennett signed a contract with Scunthorpe to run until the end of the 2023–24 season.[53] He said that he had a point to prove at the club and felt that there was a different vibe to the club.[54] He made three appearances without scoring, though did score a goal in a further appearance against Buxton which was expunged following the game's abandonment.[55] On 7 November 2023, he joined National League North rivals Southport on a three-month loan deal.[56] He scored eight goals in 28 league games for Southport in the 2023–24 campaign.[2] Scunthorpe released him at the end of the 2023–24 season.[57]
Scarborough Athletic
On 25 June 2024, Bennett joined National League North side Scarborough Athletic.[58] He scored 10 goals in 45 appearances across the 2024–25 campaign.[2] He scored five goals from 26 league games in the 2025–26 campaign.[59] He was a substitute in the play-off quarter-final defeat to Buxton.[60]