Biggest January transfers in soccer history: Football's top 10 most expensive midseason deals — and whether they worked out

The January transfer window is often a barren landscape of bit-part players and disgruntled wantaways, but it seems every year there are one or two major deals for drama-starved football fans to latch on to.

Every year, a few clubs desperate to patch up the squad or rushing to swoop for a young prodigy before anyone else strike big-money moves in the hope they can position themselves for future improvement.

While many clubs are wary of opening the coffers and spending huge sums in the middle of a campaign, every so often they throw caution to the wind. These deals tend to work out well for some, and not for others.

AllSportsPeople lists the 10 most expensive January transfer deals ever struck, with the Premier League unsurprisingly at the forefront of the activity.

MORE: Explaining why it's so difficult to strike a deal in the January transfer window 

Biggest January transfers in soccer history

The most expensive January transfer ever was the 2018 midseason move by Philippe Coutinho when he left Liverpool and joined Barcelona.

Given the money, pedigree, and expectations, the transfer is widely considered one of the biggest flops in modern history.

*Details as per Transfermarkt

*Pulisic deal completed in January, but loaned back to Borussia Dortmund for the remainder of the season

Football's 10 most expensive midseason deals — and whether they worked out

Philippe Coutinho

Having been named to the 30-man shortlist for the Ballon d'Or the year prior alongside teammate Sadio Mane, Philippe Coutinho had racked up 55 goals and 44 assists across 201 appearances for Liverpool at the time of his departure. Moving for an astonishing €131 million (the fee was inflated thanks to Neymar's world-record move from Barca to Paris Saint-Germain), the Brazilian proceeded to see his career completely fall apart.

MORE: Neymar and the most expensive transfers in football history

Coutinho would manage just 20 goals over his first two seasons with the La Liga club across all competitions before being sent to Bayern Munich on loan for a year. He would return to Catalonia for another two years of poor form until the club could no longer justify his presence. He was sold to Aston Villa for just €20 million in the summer of 2022.

It's believed that the move for Coutinho was a contributing factor to Barcelona's subsequent financial crisis, which led to Lionel Messi's departure and other massive issues within the European giants.

VERDICT: 2/10 — significant failure for astonishing cost

Enzo Fernandez

Chelsea appear three times on the top 10 most expensive January transfer list, chief amongst them the €121m swoop for Enzo Fernandez in early 2023.

Incredibly, Benfica were able to flip the 22-year-old Argentine midfielder in just six months, snatching him up from River Plate for €44 million half a year before they sold for more than double that price.

The jury is still out on Fernandez at Chelsea. He has undoubtedly blossomed into one of the club's most important players and is a regular for Argentina, but the Blues have yet to achieve anything truly notable since his arrival aside from the 2025 Club World Cup, on whose importance football fans disagree.

VERDICT: 6/10 — huge money for little tangible return yet, but a high quality player no doubt and more to come

Virgil van Dijk

Possibly the most notable January transfer of all time, the 2018 arrival of Virgil van Dijk at Liverpool brought one of the Premier League's all-time greatest defenders to Anfield.

Little did the Reds know at the time that the Dutchman would become the club's most important player of this generation, alongside Mohamed Salah. Under his guidance, much of it with the captain's armband around his bicep, Liverpool would win a Champions League title in 2019, two Premier League titles, an FA Cup, and two League Cups.

Van Dijk himself would be named Premier League Player of the Season in 2018/19, and later that year would find himself an astonishing second in the Ballon d'Or voting behind only Messi — an incredible achievement for a defender in the modern era.

It doesn't matter how much he cost, this is an all-timer of a deal.

VERDICT: 10/10 — goes down as one of the club's greatest ever players

Dusan Vlahovic

Even if Cristiano Ronaldo's brief hangout in Turin was far from a success, his departure left a gaping hole at the front of the Juventus attack. The year after Ronaldo left for a second stint at Manchester United, Juve saw their goal output plummet from 77 in the 2020/21 Serie A season to just 57 the following league campaign.

With the Old Lady desperate to recapture their huge success of the previous decade, they splashed for Fiorentina striker Dusan Vlahovic, who had scored 21 goals the previous league season and was already sitting on 17 at the time he made the midseason switch in early 2022.

Vlahovic has since been entrenched at the head of the Juventus attack, but he hasn't come close to meeting the expectations set by his massive €84m midseason price tag. The Serbia international is still just 25, but at this point it seems his ceiling was far lower than the Italian giants believed.

VERDICT: 4/10 — A useful goal scorer with a few big moments, but overall has fallen well short of the price tag

Mykhaylo Mudryk

When Chelsea moved for little-known rising Ukrainian star Mykhaylo Mudryk in January of 2023 for a shocking €70m fee, Premier League fans couldn't wait for him to fail. It seemed opposition supporters were ready to pounce on any slip in form or indication that he might not be what Chelsea had hoped.

They got their wish. Mudryk's first few Chelsea appearances showed promise, but the end product never came. He finished his first half-season at Stamford Bridge infamously without a single Premier League goal, and bagged just five across 31 appearances the following season.

Then, Mudryk tested positive for a banned substance in December of 2024 and was immediately banned by the English FA. He was officially charged with a doping offence in June of 2025, and the case is ongoing over a year after his initial suspension. Mudryk insists he did not knowingly take a banned substance.

VERDICT: 0/10 — Unless something astonishing happens, Chelsea flushed €70m down the toilet