Norwich City Middleton joined
Norwich City's Academy in 2012, graduating through their
youth system. He was given the squad number 43 for the first team during the 2017–18 season and was also named in the squad as a substitute in a
FA Cup 3rd round match against
Southampton on 18 January 2017.
Rangers Having found his senior opportunities limited at Norwich City, Middleton joined
Rangers on 31 January 2018, reuniting with former
Canaries youth coach
Graeme Murty who was the
Gers manager at the time of his arrival. with Middleton being widely praised for his performance on his debut. He scored his first goal for Rangers when he came on as a substitute in a 4–0 win against
Dundee two months later. On 26 October, Middleton signed a five-year contract with Rangers that tied him to the club until the summer of 2023.
2019–20: Loans to Hibernian and Bradford Middleton was loaned to
Hibernian in August 2019. He made eight appearances for Hibernian, but none after 30 October, and the loan was curtailed on 27 December. He was then loaned to
Bradford City on 31 January 2020 for the rest of the season.
2021–2022: Loans at St Johnstone On 25 January 2021, Middleton joined
St Johnstone on loan for the remainder of the season. He was cup-tied and missed out on their victory in the
2020–21 Scottish League Cup, but then featured as the
Saints also won the
2020–21 Scottish Cup.
Dundee United In July 2022, Middleton joined
Dundee United from Rangers for an undisclosed transfer fee, on a three-year contract.
Doncaster Rovers On 3 June 2025, it was announced that Middleton would join newly-promoted
EFL League One club
Doncaster Rovers on 1 July 2025, after his Dundee United contract expired. On 2 August 2025, Middleton made his first competitive appearance for Doncaster against
Exeter City On 1 January 2026, Middleton scored his first goal for Doncaster, netting in the 54th minute of a 1–1 draw with
Bolton Wanderers at the
Eco-Power Stadium On 29 April 2026, it was announced that Middleton had been made available for transfer. ==International career==