Born on New Year's Day in 2000 and currently trapped in the throes of a quarter-life crisis, Glenn Middleton shunned his native England to earn his corn as a journeyman winger in the uncompromising world of Scottish football. Despite standing only 1.76m (5ft 9in) tall and tipping the scales at a minuscule 68kg (10st 9lb), his slight stature belies a tenacity that has seen him establish himself as Dundee United's go-to left winger, proudly sporting the number 15 jersey.
Seemingly defying the gravitational pull of inflation, Middleton's market value hovers around a mere £300k, according to Transfermarkt, which may indeed set some hearts aflutter amongst the thrifty club owners of the sporting world. Eyes will be fixed keenly on the ticking clock as his Dundee United contract races towards oblivion, due to expire on 31 May 2025.
After cutting his teeth with Norwich City as a wet-behind-the-ears trainee back in July 2012, Middleton traded the Canaries for Rangers in January 2018, with the transfer fee spirited carefully away behind a veil of secrecy. For those who care about such minutiae, in his debut season (2018 - 2019) with the Light Blues, he graced the pitch for a grand total of 15 first team league appearances, yielding a goals-to-game ratio so minuscule it borders on statistical anonymity - just 2 goals.
Notoriously fickle, Middleton traded the blue half of Glasgow for Edinburgh, as he embarked on a temporary sojourn with Hibernian on loan in August 2019. With six first team appearances in the league, one could almost write his Hibernian memoirs on the back of a postcard. Back to Rangers in January 2020 he went, following the expiration of his Hibernian loan.
In an apparent case of chronic indecisiveness, in the same month, our protagonist decided to sample the footballing delights of Bradford City on loan. But as per his previous ventures, his seemly saccharine affair with the Bantams ended in June 2020, seeing him return to Rangers upon completion of his loan.
As if scraping the bottom of the engagement barrel wasn’t enough, Middleton then embarked on yet another loan spell, this time to St Johnstone, in January 2021. However, statistical improvement smiled upon our hero with a total of nine and then a whooping 28 first team league appearances in the 2020 -2021 and 2021 - 2022 seasons, respectively, amidst which he found the net thrice.
Having been passed around like the proverbial hot potato, Middleton eventually settled at Dundee United in July 2022, again for an undisclosed fee. Over the next three seasons (2022 - 2023, 2023 - 2024, and the ongoing 2024 – 2025), he has made a total of 91 first team appearances and scored eight goals.
In addition to mediocre league performances, our tireless winger has also graced the League Cup and Scottish Cup competitions in the 2024 - 2025 season with Dundee United, clocking six and one appearances respectively. His unique affinity for the substitute bench continues to astound footballing savants globally.
