Premier League's 20 biggest flops ever (Ranked) | OneFootball

Highlights

As with any league in world football, English fans have experienced the good, the bad, and the downright ugly. While most professional football is usually played at a standard beyond the reach of the average person, there have been a number of players over the years who have brought that statement into disrepute.

These are the players who perhaps wouldn't look out of place turning out for a national league club, or worse still, a Sunday league side. There have been countless flops that have sported the Premier League badge on their sleeve over the last three decades. With that in mind, GIVEMESPORT has decided to rank the very worst of them...

20 Marco Boogers - West Ham United

Harry Redknapp signed the unfortunately named Marco Boogers from Sparta Rotterdam for £1 million after watching a video of him in action. As scouting goes, that's not necessarily how it's done, and Redknapp was left to wish he'd watched another video instead after Boogers was sent off in just his second game for West Ham.

Following his horrendous start to life as a Hammer, the player brought in from Sparta Rotterdam, staged arguably the biggest disappearing act of them all when he was given permission to return to Holland for the birth of his son, and never came back.

19 Andy van der Meyde - Everton

Andy van der Meyde's struggles off the pitch during his time at Everton contributed to him playing just 24 games over four years with the Toffees. The Dutchman's time on Merseyside was tumultuous, to say the least; he had issues with alcohol, his dog was stolen during a burglary, his drink was spiked in a bar and his wife even hired a private detective to follow him at one stage.

It's safe to say the odds were never in his favour, with Everton consequently allowing Van der Meyde's contract to run out following a series of run-ins with manager David Moyes. He actually wanted to sign for Monaco instead but ended up in "rainy Liverpool" instead as his wife could bring her Zebra along with her to England but not to the French league. Bizzare.

18 Harry Maguire - Manchester United

Having risen through the ranks at Sheffield United, Harry Maguire’s route to the upper echelons of the football pyramid was a result of hard work, dedication, and incremental improvement season after season. After a standout display during England’s 2018 World Cup run, Maguire would land a move to Manchester United for a world record fee for a defender at the time.

Although he was made the club captain, Maguire’s time in Manchester has become one full of forgettable moments and repeated errors. Having reached rock bottom in recent seasons, it feels as though the only way from here can be upwards. Even so, the England centre-half’s susceptibility to mistakes has been his primary downfall and one that brings the £80 million sum paid for him massively into question.

17 Afonso Alves - Middlesbrough

Middlesbrough had to wait two months before Afonso Alves scored his first goal for the club after they paid a club record £14 million to sign him in January 2008. A hat-trick against Manchester City on the final day of the 2007/08 season suggested the following season would be better but that didn't prove to be the case.

Indeed, the following term he scored just four times and Boro would see themselves relegated from the top flight partly as a consequence of his inability to find the back of the net on a regular basis. This was a truly disastrous bit of business for the club.

16 Massimo Taibi - Manchester United

Sir Alex Ferguson realised Massimo Taibi wasn't the solution in goal after just four games at Old Trafford. The unconvincing Italian shot-stopper, who cost £4.5 million, produced a series of high-profile mistakes that he never quite lived down. He left just six months after arriving in Manchester.

He will always be synonymous with terrible transfers within the English game. The Sun cruelly dubbed him "The Blind Venetian" and it's safe to say he was not the Peter Schmeichel replacement the Red Devils were hoping for.

15

Jo was brought in for a club-record fee of £18 million in July 2008, just before Sheikh Mansour's takeover that would see Manchester City become a dominant force domestically and continentally. Despite arriving in the North West with that quintessentially Brazilian reputation for being a man of classy flair, the striker failed to impress.

Yes, the attacker mustered just one league goal, before being loaned to Everton twice over the course of three seasons. He certainly won't be remembered as fondly as some of the more prolific City forwards to have played for the club over the past decade or so.

Thomas Brolin admitted to being overweight when he joined Leeds United in 1995 and that contributed to a disappointing spell at the club. The Swede, who cost £4.5 million, scored four goals in 26 appearances across two seasons.

He is well-remembred for an awful performance against Liverpool but later told The Guardian he deliberately played poorly in protest of being played out of position. At the age of 28, Brolin quit football and became a vacuum cleaner salesman. That probably tells you all you need to know about his time at Elland Road.

13 Jack Rodwell - Sunderland

Jack Rodwell is to Sunderland fans what Judas was to Jesus; a traitor. The midfielder signed for Manchester City back in 2012 for £12 million, yet following a spell hampered by underperformance and injury the ex-Everton man was quickly shipped on to Sunderland, with the Sky Blues recouping £10 million of the £12 million originally spent.

Rodwell's time on Wearside was just an elongated repeat of his stint at City, with injuries and lack of commitment hampering any chance of progression. It all eventually came to an acrimonious end with the Black Cats, as the player refused to leave while picking up a wage of £70,000 a week, with the Mackems languishing in League One and financially hamstrung.

12 Timo Werner - Chelsea

Arriving in West London after snubbing Liverpool and Jurgen Klopp’s advances, big things were expected of the £47 million striker from RB Leipzig. Timo Werner had been scoring goals for fun in the Bundesliga, and his raw pace and clinical propensities in front of goal were identified by then-manager Frank Lampard as exactly what was needed to remedy the Blues deficiencies up top.

Unfortunately, Werner’s six-goal return in 35 league appearances was the best it was going to get for the striker, reduced to just four the following season, having been limited to several substitute cameos, and 15 relatively fruitless starts. The summer of 2022 would see the marksman return to RB Leipzig for just under half the amount he was sold for.

11 Kleberson - Manchester United

Brought in by Sir Alex Ferguson under the impression that Kleberson would be the natural heir to the throne left by Roy Keane, this was perhaps one of Fergie's biggest mishaps during his decorated 27 years with the club. It quickly became apparent that the Brazilian couldn't live up to the hype, and was nowhere near the level of his fiery Irish predecessor.

The central midfielder would go on to last just two seasons at Old Trafford before being offloaded to Turkish outfit Beşiktaş. He actually only joined the Red Devils because he thought Ronaldinho was heading that way too. What a mess...

10 Andriy Shevchenko - Chelsea

Andriy Shevchenko wasn't the player Chelsea – indeed, the entire league – thought he would be. The Ukrainian international had been immense during the preceding years at clubs like AC Milan, but his three years at Chelsea following the Blues' £30.8 million investment returned little by way of value for money.

The striker managed just 22 goals in 77 games, a dismal showing for a player famous for his potent ability in front of goal. While he impressed so many in Italy, for most in England he is best remembered for being one of many strikers who failed to make the grade at Stamford Bridge.

9 Jadon Sancho - Manchester United

There is still technically time for the former Borussia Dortmund star to turn things around at Old Trafford but having publically fallen out with Erik ten Hag, the writing appears to be on the wall for Jadon Sancho at Manchester United.

If he is to leave, fans will be left mourning a talent that just never burst into life on English shores. After all, he earned a reputation as one of the most dazzling wingers in the world during his time in Germany but with nine goals and six assists in 59 league outings for the Red Devils, Sancho has mostly disappointed.

8 Adrian Mutu - Chelsea

Chelsea have had a lot of attacking players over the years who have failed to live up to experience. After all, there is the famous No. 9 shirt curse that has curtailed many careers at Stamford Bridge. Adrian Mutu, however, did not wear that kit number and yet perhaps flopped harder than any – though not entirely for what he did on the pitch.

The striker tested positive for cocaine and was banned from the sport for seven months. Consequently, the Blues decided to tear up his contract and sued Mutu for breach of contract. They won the court case, as FIFA dished out the biggest financial penalty to a player in their history when the governing body ruled that he owed Chelsea £15.2 million.

7 Fernando Torres - Chelsea

Talking of Chelsea forwards who did anything but flourish in West London, we have Fernando Torres next up on this list. He may have managed 45 goals in 172 games for the Blues, not totally awful, but having scored 81 in 142 for Liverpool, it's clear to see just how much he dropped off.

It actually took the Spaniard 903 minutes of football to score his first goal for Chelsea and it felt as though he was always playing with some weight upon his shoulders. Having cost £50m, it never really looked like money well spent.

Unfortunately for Nicolas Pépé, he was signed in an era of ever-increasing transfer fees and so the bar was raised nice and high for him in north London before he'd even kicked a ball. Indeed, the Gunners splashed £72 million on the winger in what was a club-record transfer fee at the time.

Unfortunately, the Ivorian always looked like an awkward fit at Arsenal and struggled to convince both Unai Emery and then Mikel Arteta. The emergence of Bukayo Saka left Pépé surplus to requirements and he departed in 2023, leaving for free, having scored 27 goals in 112 appearances.

5

After lighting up St. James' Park with Newcastle United, Andy Carroll was rewarded for his performances with a move to Liverpool. The tall Geordie, with his unmistakable ponytail, found the net on just 11 instances for Liverpool, a measly return on his £35 million transfer fee in 2012.

However, the Reds and Kenny Dalglish did get it right with their cheaper acquisition of Luis Suárez on the same day, who cost them just £23 million. Unfortunately, though, the Uruguayan's excellence only helped paint a poorer picture of Carroll and his time at Anfield.

4

Sir Alex Ferguson signed Bebé for £7.4 million in 2010 without ever seeing him play, and it would prove to be a serious mistake. Bebe was one of Man United's worst-ever players. In a game against Wolves, for instance, he replaced Owen Hargreaves as an early substitute before being hooked off himself in the second half.

The striker played just two times in the Premier League for the Red Devils, failing to score a goal. Unsurprisingly, Ferguson wanted none of the responsibility for signing Bebé, instead blaming his assistant Carlos Queiroz. He spent most of his time out on loan but still stayed contracted at United for four years.

3

The Blues already had a pretty good idea of just how good Romelu Lukaku could be when they signed him from Inter Milan for £97.5 million. After all, he'd already enjoyed three years with them, albeit most of that time was spent out on loan banging in the goal for Everton and West Brom.

When he returned in 2021, Chelsea were expecting the finished product at Stamford Bridge, the man who'd just fired Inter Milan to the Serie A title with 24 goals. Instead, they got a completely underwhelming forward who scored just eight league goals before returning to Italy the next summer.

In the summer of 2022, Erik ten Hag left Ajax for Manchester United. In Lisandro Martinez and Antony, the Dutch manager brought with him two other fellow men from Amsterdam. The Brazilian cost a mammoth £86 million and so arrived with higher expectations. It's safe to say, however, he's not lived up to them since.

The winger did net a goal against Arsenal on debut but that appeared to be a false dawn. Indeed, in his first 53 appearances for the Red Devils, Antony has provided a paltry eight goals and three assists. Lacking key attributes such as pace, vision, or a clinical touch, it's hard to see why United felt he would be worth spending so much money on – that massive fee is why he ranks so poorly on this list.

1 Ali Dia - Southampton

The story of Ali Dia playing for Southampton is truly iconic. He managed to fool the Saints into believing he was George Weah's cousin and had previously played for Paris Saint-Germain. What's more, he blagged a short contract with the club and even played 53 minutes for them against Leeds in 1996, making it clear to then-boss Graeme Sounnes that he was more of a conman than he was a footballer.

Southampton's players thought Dia had won a competition to train with the Saints, which says it all about his ability. He may not have cost as much as some of the other flops on this list, but his transfer is just so bizarre, the Senegalese striker deserves his spot in first place. At least the others named above could pass as Premier League footballers for more than just one appearance!