The six worst Premier League transfer windows of all time – including Chelsea & Liverpool nightmares

Another transfer window has slammed shut, as they are wont to do, and before too long we’ll learn which teams have brilliantly navigated the choppy waters of modern football business and which have signed a bunch of hopeless duffers. We’ll even get to find out whether Chelsea made a single sensible decision.

If history is any guide, at least a few teams will turn out to have made a complete hash of it. There’s no shortage of squads made worse by a summer’s wheeling and dealing – so here are the six worst transfer windows in Premier League history, the teams who had all the wrong plans, signed all the wrong players, and ended up setting things back, often by several seasons…

Chelsea 2022

It’s only right and proper that we start at Stamford Bridge, now the spiritual home of the questionable signing – and it didn’t take long for Todd Boehly and company to start making dodgy decisions, as we can see by casting our memories back to the current owners’ very first transfer window in the summer of 2022.

Over £250m of players arrived right away, and while many of the more infamous mistakes were yet to come, there were plenty of flops right from the beginning. There was some bad lucky in there – nobody could have known that the wildly expensive Wesley Fofana would be struck down by a string of serious injuries, for instance, and it wasn’t unreasonable to expect Raheem Sterling and Kalidou Koulibaly to be rather better for Chelsea than they were, but Marc Cucurella for nearly £55m? £10m on a patently past-it Pierre-Emerick Aubameyang?

In fairness to Boehly and his chums at Clearlake Capital, it’s not like the Roman Abramovich era didn’t feature some seriously wayward splurges, where it was the summer of 2017 when they spent north of £85m combined on Danny Drinkwater, Davide Zappacosta and Tiemoué Bakayoko, or that first spending spree which brought such luminaries as Alexei Smertin to Stamford Bridge. But for sheer volume of dodgy spending, 2022 takes some beating.

Everton 2017

How do you replace your big-money star striker? Not by buying every number ten under the sun, if Everton are any guide. Tasked with filling the sizeable shoes of the departed Romelu Lukaku, the Toffees simply went a bit mad, spending over £60m on Davy Klaasen, Gylfi Sigurðsson and Sandro Ramírez, none of whom did anything worth writing home about during their time at Goodison Park.

In fairness, the return of Wayne Rooney on a free transfer did work out a little better for them, albeit briefly, and they bagged Jordan Pickford as well, but this is a window mostly notable for the pretty disastrous reinvestment of a windfall. Everton still finished in the top half for the next two seasons, but it was the start of the backsliding which resulted in a couple of brushes with relegation.

Newcastle United 2012

Sometimes, the worst thing you can do isn’t signing a bunch of bad players, but barely signing any players at all. That’s what Newcastle did shortly after Alan Pardew had earned them European qualification in the 2011/12 season – faced with the prospect of playing twice a week after their fifth-place finish, the ever-munificent Mike Ashley dipped into his wallet and came up with just enough cash to buy Vurnon Anita, who flopped, and a couple of kids, who eventually flopped as well.

Newcastle finished 16th and immediately found themselves going from European contenders to relegation battlers while Pardew started headbutting players on the pitch. Well, OK, just one player, but it’s one more than any other Premier League manager to date. The Magpies aren’t the only team to do nothing in a transfer window and regret it, either – back in 2015, Arsenal added Petr Cech and nobody else all summer and ended up finishing ten points short of shock champions Leicester City. Had they invested and improved, who knows what could have been?

Burnley 2023

To be fair to Newcastle and Arsenal, perhaps being risk-averse isn’t always such a terrible idea. Just take a look at Vincent Kompany’s Burnley last season, who stormed the Championship to earn promotion and then took the bold decision to completely replace their successful squad with a bunch of kids.

No fewer than 15 new players arrived at Turf Moor for a total investment of over £90m, most of them very green around the ears, and one suspects that even the most ardent Burnley will struggle to name most of them in ten years’ time. Hannes Delcroix, anyone? Mike Trésor. At least Wilson Odobert was eventually sold on for a healthy profit and Luca Koleosho will probably make some money as well, but that doesn’t really make up for an immediate relegation.

Liverpool 2002

Liverpool have had a few stinkers in their time, but there were usually some extenuating circumstances and even the window which saw them spend a colossal amount of cash on Andy Carroll also brought Luis Suárez to the club – but the start of the 2002/03 season saw them fritter their budget away on a string of players who left very few good memories at Anfield.

The problem was that Liverpool’s transfer team boarded a bunch of hype trains that turned out to be going nowhere. Fresh off the back of Senegal’s remarkable run to the quarter-finals of the World Cup in Japan and South Korea, about £19m (big money at the time) was dropped on El-Hadji Diouf and Salif Diao, neither of which could maintain their performances from a golden summer, while Bruno Cheyrou, Anthony Le Tallec and Patric Luzi were all promising young French players who never came close to living up to their alleged potential. To make matters worse, all these underwhelming young bucks arrived after losing experienced heads Gary McAllister, Jamie Redknapp, Jari Litmanen and Nicky Barmby. Those who left were rather better than those who arrived, and Liverpool wouldn’t seriously challenge for the Premier League for years to come.

Manchester United 2015

The post-Ferguson years have yet to be kind to the Red Devils, at least in the league. They won the FA Cup off the back of Louis van Gaal’s summer spending ahead of the 2015/16 season, but most of the players that arrived that year won’t live long in the memory, at least not for the right reasons.

Anthony Martial did have a couple of good seasons before his long decline and there were some flashes from an over-the-hill Bastian Schweinsteiger, but £30m on Morgan Schneiderlin looks laughable in retrospect, Memphis Depay managed just two league goals for the club and Matteo Darmian sort of just hung about Salford for a few years, doing very little memorable. This was also the summer that Robin van Persie, Javier Hernández, Nani and Ángel di Maria all left, and the gradual drain of talent following Sir Alex’s glittering tenure was all but completed.