The 2026 winter transfer window has already welcomed one new addition to the all-time top 10 list, as Antoine Semenyo's £64m switch to Manchester City from Bournemouth made him the seventh biggest mid-season mover in history.
The highly-anticipated deadline day is now looming - February 2 is the cut-off point for Premier League clubs this year - and while there may not be as many twists and turns as the summer window, big-money moves are never off the table.
Ahead of this winter's transfer deadline day, Sports Mole counts down the top 10 biggest January deadline-day deals of all time.
10. Andre Schurrle
Club: Wolfsburg
Year: 2015
Fee: £27.7m
After a modest couple of years at Chelsea, German winger Andre Schurrle departed for Wolfsburg in early February 2015, but he would continue his trend of flip-flapping between numerous clubs.
Stints at Borussia Dortmund, Fulham and Spartak Moscow followed for the winger before his premature retirement in 2020, six years after his most notable contribution - the assist for Mario Gotze's winner in the 2014 World Cup final.
9. Willian
Club: Anzhi Makhachkala
Year: 2013
Fee: £30.4m
Willian made a name for himself in Ukraine before joining Russian outfit Anzhi Makhachkala for £30.4m in early 2013, but he would spend just one-half season with the club before his marquee move to Chelsea.
Two Premier League titles and a disastrous spell at Arsenal later, Willian - who also represented Fulham for a brief period - is still going strong in his homeland, signing for Gremio in the summer of 2025.
8. Andy Carroll
Club: Liverpool
Year: 2011
Fee: £35.5m
In the first half of the 2010-11 season, Andy Carroll registered 19 goal contributions in 19 games for Newcastle United, form that convinced Liverpool to take a £35m punt on the Englishman in late January.
However, the injury-plagued striker managed just 11 goals in 58 games for the Reds, and he can now be found in the National League with Dagenham & Redbridge following spells at Reading, Amiens, Bordeaux, West Ham United and West Bromwich Albion.
7. Jackson Martinez
Club: Guangzhou Evergrande
Year: 2016
Fee: £36.4m
One for the old-school FIFA players out there, Colombian striker Jackson Martinez was one of the big movers to China in 2016, when his move to Guangzhou Evergrande banked Atletico Madrid £36.4m.
That transfer worked out at £9.1m per goal - you do the maths - and Martinez hung up his boots in 2020 following a brief return to Portuguese football.
6 Galeno
Club: Al-Ahli
Year: 2025
Fee: £43.4m
Another South American attacker who burst onto the scene with Porto, Galeno was tempted by the Saudi Arabian riches and signed for Al-Ahli for £43.4m on the Pro League's winter deadline day last year.
The Brazilian took little time to settle in, registering seven goal contributions in seven AFC Champions League matches last season as Al-Ahli took home the continental title.
5. Fernando Torres
Club: Chelsea
Year: 2011
Fee: £50.7m
Chelsea failed with a £40m bid for Fernando Torres in 2011 before seeing a £50.7m offer accepted on deadline day, after which his time at Stamford Bridge was famed for one high-profile miss and one high-profile goal.
Torres's Old Trafford howler and Barcelona tap-in live on in football folklore, and the former Spain striker is now working as a youth coach with Atletico Madrid following his 2019 retirement.
4. Nico Gonzalez
Club: Manchester City
Year: 2025
Fee: £52m
Thrown into the deep end at the Etihad Stadium, Nico Gonzalez joined Manchester City in early 2025, a few months after Ballon d'Or winner Rodri suffered his devastating ACL tear.
The 24-year-old has some way to go to hit the heights of his compatriot, but he has now acclimatised to Pep Guardiola's system and has become a key player for the Sky Blues.
3. Pierre-Emerick Aubameyang
Club: Arsenal
Year: 2018
Fee: £55.3m
Arsenal's last signing of the Arsene Wenger era, Pierre-Emerick Aubameyang enjoyed a goal-laden, front flip-filled four years at the Emirates after his £55.3m transfer from Borussia Dortmund on deadline day 2018.
Consistency has been hard to come by for the Gabon international since his acrimonious exit in 2022, but he has now found safe haven with Roberto De Zerbi's Marseille.
2. Jhon Duran
Club: Al-Nassr
Year: 2025
Fee: £66.8m
With just hours to go in the 2025 winter Saudi Pro League window, Aston Villa accepted a mammoth £66.8m offer from Cristiano Ronaldo's Al-Nassr for Jhon Duran, the super sub of all super subs.
Despite scoring 12 goals in his first 18 games for Al-Nassr, Duran was soon lured back to Europe with Fenerbahce on loan, and the 2003-born striker still has plenty of years left in his legs.
1. Enzo Fernandez
Club: Chelsea
Year: 2023
Fee: £104.9m
The second-most expensive January deal of all time - only trailing Philippe Coutinho to Barcelona - Chelsea finally got their man in January 2023, writing out a nine-figure cheque to Benfica for Enzo Fernandez.
The Argentine struggled to justify his price tag initially, but he has now established a reputation as a masterful midfield metronome, thanks to his eye for goal and stellar passing range.