Born in Ashington, Middleton began karting at the age of six, during which he won the Ginetta Junior Scholarship in late 2014 to secure a fully-funded drive for the following year's Ginetta Junior Championship. Racing for Douglas Motorsport in his rookie season, Middleton finished third at Thruxton from pole, before taking a pair of second-place finishes at Rockingham to end the year seventh in the overall standings. After winning the Winter Series title in late 2015, Middleton returned to Douglas for the 2016 season. In his second campaign, Middleton took five wins in the first five rounds, including a double at Croft, and then won twice more after the summer break to secure runner-up honours behind Will Tregurtha.
In 2017, Middleton moved up to the GT4 class of the British GT Championship for HHC Motorsport, sharing a Ginetta G55 GT4 with Ginetta Juniors title rival Tregurtha. In his maiden season in the series, Middleton scored overall GT4 wins at Rockingham and Snetterton, and took five other podiums to clinch the overall and Silver Cup titles. Towards the end of the year, Middleton won the SunocoWhelen Challenge, earning him a fully-funded drive at the 2018 24 Hours of Daytona for Action Express Racing's Prototype squad. On his IMSA debut, Middleton finished second at the Floridian enduro in the team's Cadillac DPi-V.R, alongside Mike Conway, Eric Curran and Felipe Nasr. For the rest of the year, Middleton returned to HHC Motorsport to enter the GT4 European Series alongside Tregurtha. In his only season in the series, Middleton took wins at Zolder and Brands Hatch, as well as four other podiums to clinch runner-up honours in the Silver Cup on countback, as the top three all finished level on points.
Moving to Lamborghini Super Trofeo Europe with Bonaldi Motorsport, Middleton began 2019 with a win at Silverstone, before taking further wins at Spa and Jerez to end the year third in the Pro standings alongside Jack Bartholomew. Switching to its North American counter part with Prestige Performance/Wayne Taylor Racing for 2020, as part of the Lamborghini Young Driver Programme, Middleton took six podiums to end the year fourth among the Pro entries alongside Stevan McAleer.
Graduating to GT3 for 2021, Middleton joined Imperiale Racing to race a Lamborghini Huracán GT3 Evo in the Italian GT Championship Endurance Cup alongside Andrea Amici and Alberto Di Folco. The trio won at Mugello and missed the podium only once in the four-race season to clinch runner-up honours overall. In 2022, Middleton remained with Di Folco to race for Imperiale in Italian GT's Sprint Cup. At the start of the season at Monza, Middleton was hit by another car during the driver change procedure in race one, leaving him with multiple injuries and unable to compete in race two. Returning for the following round at Misano, Middleton bounced back with wins at Imola and Mugello to end the year sixth in the overall standings, two spots behind Di Folco.
Teaming up with Kevin Gilardoni and Raúl Guzmán at Imperiale for 2023, Middleton returned to the Italian GT Endurance Cup and won the finale at Vallelunga to end the year third overall. In parallel, Middleton also raced in the GT4 class of the British GT Championship for Raceway Motorsport, sharing a Ginetta G56 GT4 with Freddie Tomlinson, son of Ginetta chairman Lawrence Tomlinson. The pair finished 10th in points with a lone win at Snetterton. In 2024, Middleton made sporadic appearances in the series in Ginetta machinery for Team CMR and DTO Motorsport, most notably qualifying on pole at the first Donington Park enduro for the latter.
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