Liverpool and Arne Slot looked set to grab the Premier League and become the dominant force in the country when they splashed £450million, broke the British transfer record twice in as many weeks with Alexander Isak (£125m) and Florian Wirtz (£116m), as well as signing Hugo Ekitike for £75m, just weeks after winning the league at a canter.
But it all fell apart as the Reds just about secured Champions League football on the final day ahead of Bournemouth and Slot was given the chop as the Reds ended the campaign 25 points behind champions Arsenal. That failure saw Jamie Carragher brand Liverpool’s 2025/26 season as “arguably the worst transfer window we’ve probably seen in Premier League history, when you consider the fees for these players, and what it’s going to do for Liverpool.”
And Manchester United’s window of two years prior in the summer of 2023 will be very thankful the shine was taken off them after Erik ten Hag splurged over £200m – £72m of that on Rasmus Hojlund, £47.2m on Andre Onana and £55m on Mason Mount – who took two years to play 90 minutes due to persistent injuries. United won the FA Cup, but no thanks to any of the signings, and Ten Hag was sacked months later after the Wembley triumph provided him a stay of execution.
Liverpool’s 02/03 window will give anything a run for its money after Gerard Houllier shopped exclusively in France as he looked to take the Reds one better than a 2nd place finish the previous season following the cup treble the campaign prior. But signing El-Hadji Diouf, Salif Diao, Bruno Cheyrou and Anthony Le Tallec, while snubbing the chance to sign Nicolas Anelka permanently was a key reason in the club failing to qualify for the Champions League that year.
Spurs sold Gareth Bale for a world record £86million, and proceeded to splash more than £100m on flops Paulinho, Nacer Chadli, Roberto Soldado, Etienne Capoue, Vlad Chiriches and Erik Lamela – with only Christian Eriksen of the sarcastically labelled ‘magnificent seven’ proving a good signing.
This is arguably the beginning of United’s downfall, which was merely delayed by Sir Alex Ferguson’s brilliance. The Premier League champions and Champions League finalists sold superstar Cristiano Ronaldo to Real Madrid for £80million and let Carlos Tevez head to Manchester City, while signing past it free agent Michael Owen, Gabriel Obertan, Mame Biram Diouf and the best of the bunch, Antonio Valencia, as their replacements. Oh dear.
Manchester City rarely ever get it wrong in the transfer market, but they endured a horrible window trying to build their first defending title side. Roberto Mancini added flops Jack Rodwell, Scott Sinclair, Maicon, Matija Nastasic and Javi Garcia – to lose the title to United by 11 points.
Everton fans couldn’t believe their eyes as the club shelled out more than £180m but to absolutely no avail. Davy Klaassen, Sandro, Gylfi Sigurdsson, Nikola Vlasic, Theo Walcott and Cenk Tosun all failed and were shipped out at huge deficits, while calamity-ridden Michael Keane and England goalkeeper Jordan Pickford still remain at the club. The Toffees have never finished higher than 7th place since they splurged the cash – and it couldn’t have left them in more trouble.
Arsene Wenger had seen Cesc Fabregas, Samir Nasri and Gael Clichy leave in the summer of 2011, the former to Barcelona and the latter pair to emerging rivals Manchester City, and the Gunners miserably signed Mikel Arteta, Gervinho and Andre Santos as their replacements, seeing Arsenal infamously beaten 8-2 by Manchester United at Old Trafford.
Alan Pardew led the Magpies to a 5th place finish the season prior, and hopes of building on that were soon scuppered as Vurnon Anita and Gael Bigirimana were the pick of summer signings. The French revolution on Tyneside began with five Frenchmen added in January – but the Toon fell to a 16th place finish and were relegated just three years later.
Champions Chelsea became a laughing stock the following season, as Antonio Conte added Tiemoue Bakayoko, Danny Drinkwater, Antonio Rudiger, Davide Zappacosta and Alvaro Morata to his side for a combined £185m. The Blues finished 5th in the 17/18 campaign and three of the signings later left as free agents.
An incredible send off to Upton Park saw West Ham move into the London Stadium playing Europa League football. But the nightmare debut campaign started as the club failed to qualify for the group stages in Europe while 16 players were signed – including Andre Ayew for £20m and Robert Snodgrass for £10.2m. It was made worse in January as star man Dimitri Payet forced a move back to Marseille as the Irons finished in 11th.
Possibly the worst window in the club’s history left Liverpool at their lowest for decades. Jonjo Shelvey, Milan Jovanovic, Danny Wilson, Joe Cole, Christian Poulsen, Brad Jones, Raul Meireles, Paul Konchesky were all signed – while flop Andy Carroll arrived in the winter for £35m. The only saving grace was the signing of Luis Suarez in January, but the Reds wouldn’t return to the Champions League for another three years.
It’s impossible to pin one Old Trafford window post Fergie, so we’ll go with the one that kicked it all off. Sir Alex had retired and David Moyes and new chief executive Ed Woodward bumbled around the offices for two months before making United’s only summer signing – Marouane Fellaini for £27.5m on deadline day – just weeks after his £23.5m buyout clause had expired. United finished 7th and Moyes got the chop.