The 11 Worst Signings in Football History [Ranked]

Football has seen an increase in transfer activity, with clubs willing to spend astronomical sums to secure the best talent from around the world. While this financial firepower has led to more deals being made, it also brings a great deal of risk.

Not every transfer lives up to the expectations of the club, the fans, or the player. High-priced flops are becoming a significant part of the sport, and as such, determining the worst football transfer in recent history is no easy task.

We've set out to answer that question by ranking the worst transfers ever. Our rankings take into account the following factors:

• Expectations upon signing
• Transfer fee
• Resale value
• Longevity at the club
• Statistical performance

Now, let's dive into some of the most disappointing transfers we've seen in football...

1. Eden Hazard to Real Madrid

Transfer fee: £103 million rising to £135 million

Eden Hazard's move to Real Madrid in 2019 quickly became one of the most underwhelming transfers in football history. In his first season in Spain, he scored just one goal, a stat that did little to ease the frustration among Madrid fans, especially after he arrived to pre-season seven kilograms overweight.

Things only got worse as Hazard was seen laughing with former Chelsea teammates after they eliminated Madrid from the Champions League, while his time in Spain was marred by persistent injuries. The winger, once hailed as one of the Premier League’s finest, never came close to replicating his former brilliance at Chelsea. After a disappointing spell in Madrid, he retired from football in 2023 at the age of 32. Given his hefty price tag, lackluster performance, and stark decline in form, Hazard's transfer to Real Madrid stands as one of the worst signings of all time.

2. Phillippe Coutinho to Barcelona

Transfer fee: £121.50 million (Approx)

It was a tough call between Coutinho and the player in third place, but ultimately, Barcelona sold the Brazilian for a staggering loss of around £100 million after one of the most disappointing transfers in history. Coutinho had dazzled in the Premier League with Liverpool and was desperate to move to Barcelona, even handing in a transfer request to make it happen.

With all the hype surrounding his blockbuster move, it’s being generous to say the Brazil international ever lived up to expectations in the iconic Barcelona shirt. His time at the club was marked by underwhelming performances, and let’s not forget the two goals he scored against them while on loan at Bayern Munich during the Champions League quarter-finals—what a slap in the face.

3. Antoine Griezmann to Barcelona

Transfer fee: £108 million

Ah, another Barcelona disaster. The first problem with this transfer was that no one wanted the club to sign Griezmann—not the players, not the manager. In reality, the deal perfectly encapsulated the chaotic state of the Barcelona board at the time.

The Frenchman arrived with a massive contract that put such a strain on the club's finances, it played a key role in the eventual departure of their crown jewel, Lionel Messi. Griezmann's time at Camp Nou was nothing short of miserable, and in the end, the board decided to loan him back to Atlético Madrid.

The kicker? The loan included an optional future fee of £54 million, which Atlético Madrid eagerly activated. You can bet Diego Simeone slept soundly that week, knowing he had just tricked Barcelona into coughing up over £50 million. A real bargain for Atlético—have some of that.

4. Romelu Lukaku to Chelsea

Transfer fee: £97.5 million

Chelsea makes another appearance on this list, as the west London club has been one of the most active teams in the transfer market over the past two decades. Romelu Lukaku was supposed to be the returning hero when Chelsea swooped to re-sign their former Belgian striker following his successful Serie A campaign with Inter Milan. The narrative was set for a fairytale return, with Lukaku expected to elevate Chelsea to a Premier League title.

However, it quickly turned into a nightmare. Lukaku lost his starting spot under Thomas Tuchel and made matters worse by giving an unsanctioned interview with Sky Italy, openly stating his desire to eventually return to Inter. Unsurprisingly, this didn't sit well with either the club or the fans, leading to Lukaku being loaned out after a dismal season at Stamford Bridge. When considering the massive financial outlay, this may go down as one of the worst signings in Premier League history.

5. Alexis Sanchez to Manchester United

Transfer fee: Free

When Alexis Sánchez made the move from Arsenal to Manchester United, he was widely regarded as one of the best players in the league. He had been a standout performer at the Emirates, and the thought of him taking charge at Old Trafford sent shivers down the spines of rivals.

However, it quickly became apparent that United's fears were misplaced. Sánchez scored just three league goals in one and a half seasons at the club. His astronomical wage of £560,000 per week became a significant burden on United, especially since much of his time was spent on the bench. Eventually, he was loaned to Inter Milan, but United continued to cover a substantial £200,000 per week of his salary. It’s fair to say that Sánchez could be considered one of the club's worst signings in history.

6. Andriy Shevchenko to Chelsea

Transfer fee: £39.5 million

Roman Abramovich had been eager to bring Andriy Shevchenko to Chelsea for years before finally securing the Ukrainian's signature in 2006. However, there was a catch: it was Abramovich's desire, not José Mourinho's. The Portuguese manager wasn't keen on Shevchenko, and that was reflected in his performances on the pitch.

The 2004 Ballon d'Or winner spent much of his Chelsea career out of position, which contributed to a disappointing return of just nine Premier League goals in 48 appearances. After two seasons at Stamford Bridge, Shevchenko was loaned back to Milan. In the end, Chelsea never got the version of the striker they had hoped for, adding to the club's long-standing struggles with number nines.

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7. Jonathan Woodgate to Real Madrid

Transfer fee: £16 million

Jonathan Woodgate's time at Real Madrid got off to an incredibly rough start. After a year sidelined with injury, the English defender returned to make a disastrous debut—scoring an own goal and being sent off. It was a nightmare scenario that could hardly have gotten worse. Unfortunately, things didn’t improve from there for Woodgate, as injuries continued to hamper his progress, and he managed only nine La Liga appearances before returning to the UK.

To make matters worse, Spanish media outlet Marca ran a poll naming him 'the worst signing of the 21st century.' Ouch, indeed.

8. Ángel Di María to Manchester United

Transfer fee: £60 million

Angel Di Maria's time at Manchester United is another high-profile transfer that failed to live up to expectations. Having been one of the most creative players in the world at Real Madrid, Di Maria was expected to make a major impact at Old Trafford. Early on, he showed glimpses of his talent, even earning the club's Player of the Month award.

However, things quickly took a turn for the worse. A hamstring injury, combined with a traumatic break-in at his house, unsettled the Argentine, and his performances dramatically declined. It became clear that Di Maria was unhappy in England, and he seized the first opportunity to leave, joining Paris Saint-Germain the following summer.

9. Andy Carroll to Liverpool

Transfer fee: £35 million

Andy Carroll was brought in to replace a player we'll mention shortly, but his time at Liverpool didn't go as expected. The towering striker had made a strong impression at Newcastle, scoring 11 goals in just 19 appearances. However, his playing style didn't align with Liverpool's tactics, making it feel like a poor fit from the start.

Carroll's struggles were compounded by being frequently left out of the starting lineup due to the exceptional form of Luis Suárez. He often looked out of place on Merseyside, managing just six goals in 44 Premier League matches before being sold to West Ham for a fraction of the original fee.

10. Fernando Torres to Chelsea

Transfer fee: £50 million

Fernando Torres' move to Chelsea remains one of the most debated transfers in modern football. The Blues paid a hefty £50 million to sign the Spaniard from Liverpool, where he had been the club's standout player for three years.

At just 26, Torres was expected to be in the prime of his career, but he struggled to replicate the dazzling form that had terrorized defences at Anfield. His goal-scoring record dropped dramatically—he went from scoring every 120 minutes at Liverpool to one every 360 minutes at Chelsea.

Although he did score a crucial away goal in the Champions League semi-final against Barcelona, that moment stood as one of the few bright spots in an otherwise underwhelming stint in London.

11. Mario Balotelli to Liverpool

Transfer fee: £16 million

Ah, Super Mario. What a character. A player brimming with potential, Mario Balotelli showed flashes of brilliance during his time at Manchester City, but his moments of genius were often overshadowed by countless instances of madness.

After a falling out with his teammates at City, he was sold to Milan, where he somewhat revived his career, netting 14 goals in Serie A. This sparked Brendan Rodgers to take a gamble on the 24-year-old, hoping to find a worthy replacement for Luis Suárez.

Although Liverpool fans were initially skeptical, Rodgers had a reputation for getting the best out of players, so there was some cautious optimism. However, that optimism quickly faded. Balotelli’s reluctance to track back, coupled with his habit of attempting audacious shots from 40 yards, led to widespread frustration. He managed just one Premier League goal in 939 minutes of play before being sent back to Milan on loan.