Football

The Biggest Premier League Flops of All Time

biggest-premier-league-flops

Football odds can cover anything from goals scored to full-time results – and everything in between. That’s half the fun of football betting and sports betting.

Some of the players below would likely have had very long Premier League odds for finding the back of the net given how poor they turned out to be for their clubs.

Romelu Lukaku

They say never go back and Chelsea learned the hard way when they gave former striker Romelu Lukaku a second chance at Stamford Bridge back in the summer of 2021. The Blues splashed out a staggering £97.5million to buy what they thought was the final piece of their jigsaw as they targeted a first Premier League crown since 2017.

The 29-year-old Belgian had guided Inter Milan to a first Serie A title in over a decade the previous campaign and just two months into his Chelsea return was publicly serenading the San Siro outfit – eventually getting his wish as he returned to Italy on a season-long loan in June 2022 and making him one of the priciest flops in Premier League history.

Timo Werner

The biggest flop in Chelsea’s Premier League history? If he isn’t, then Timo Werner isn’t too far off. Brought to the club by Frank Lampard, the German cost a not insignificant £47.5m. Like many strikers before him, he struggled with confidence in front of goal after not being able to hit the net as regularly as he’d hoped.

Much of that could be attributed to Lampard trying to shoehorn him into a position that clearly didn’t work for him. Even under Thomas Tuchel, Werner continues to struggle however. The sooner he departs Stamford Bridge, the better for all concerned.

Ali Dia

One of those transfers to be filed in the ‘you couldn’t make it up’ category. Long before the internet and mobile phones, managers relied on good old fashioned scouting or videos of players to help them make a decision. Graeme Souness, he of Sky Sports fame, was Southampton manager in 1996 when it’s claimed he received a call from former FIFA World Player of the Year, George Weah.

Supposedly, Ali Dia was his cousin and the caller somehow convinced Souness to take the bait. Dia was signed to a one-month contract, played just 21 minutes as a sub against Leeds United before being subbed himself, and was never heard from again. Grainy footage does exist of the most remarkable cameo appearance in modern football history, which is almost certainly something that Souness will never live down.

Juan Sebastian Veron

One of the biggest names in Argentinian football, Veron turned out to be one of the biggest mistakes in Sir Alex Ferguson’s tenure at Man United. He cost a British record £28m back in 2001 and his first few games earned him a Player of the Month award. That was as good as it got. Veron struggled badly with the pace of the game in England and could never really adapt to it. No one doubted his skill set and ability, but he didn’t show it often enough.

Even a move to Chelsea in 2003 didn’t work out to the satisfaction of either party meaning his entire time spent in England was nothing short of a disaster.

Adrian Mutu

The year 2003 wasn’t great for Chelsea with the Blues also counting the cost of a move for Adrian Mutu. The Romanian was a £15.8m buy but his prowess in front of goal left a lot to be desired as six goals in 27 evidenced.

It was his admittance of playing whilst high on cocaine, and subsequent sacking a year after putting pen to paper that was of far more interest to the newspapers, who delighted in taking him down. Arguably, his career never recovered.

Marco Boogers

Marco Boogers will always be fondly remembered by West Ham fans for upending Gary Neville during a game against Man United. Unfortunately for the Dutchman, that tackle earned him a red card in just his second game for the east Londoners. He’d done nothing in either game to justify his purchase in 1995, but Harry Redknapp allegedly hadn’t even seen him play before signing him, so couldn’t really have been too surprised.

Boogers only managed four substitute appearances before being sold.

Diogo Dalot

After playing less than a dozen games for Porto’s first team, spending his whole youth career at the Portuguese giants too, Manchester United evidently saw enough to splash almost £19m out in 2018 for the then 19-year-old.

Unfortunately, Dalot never came close to establishing himself at the Theatre of Dreams. Given a chance sporadically, it was no real surprise when he was loaned out to AC Milan in 2020. Now back at United, he is still in the first-team wilderness, and is likely to be so for the foreseeable future.

Francis Jeffers

As a young player at Everton, it was felt that Francis Jeffers was a real prospect and would help lead them to long overdue success. Unfortunately for the Toffees, once Arsenal came calling there was never a chance he was staying on Merseyside.

Unfortunately for Arsene Wenger, Jeffers never turned into the player that everyone expected and in three seasons he managed just four goals in 22 appearances. The Frenchman didn’t get much wrong in his 22-year tenure, but Jeffers’ signing was certainly a blot on his copybook.

Tomas Brolin

After starring at the European Championships in 1992 for Sweden, Brolin enhanced his standing at the 1994 World Cup. That tempted Howard Wilkinson to buy him for Leeds United in 1995, but the ‘Baby-faced assassin’ as supporters quickly dubbed him, started putting on weight, lost fitness and, subsequently, motivation.

Falling out with Wilkinson was always going to follow, but a bizarre turn of events involving a series of loans, fines and failed moves elsewhere meant that Brolin was still registered as a Leeds player until the club cancelled his contract on October 28, 1997.

Eric Djemba Djemba

It’s hard to believe that Sir Alex had signed Djemba Djemba as a potential long-term successor to Roy Keane. It was believed that he was just as dogged and determined in his play as the Irishman, however, he was never anywhere close to the player that United thought they were buying from Nantes.

Sold to Aston Villa at a loss, he only got to play one game as a sub in the opening match at Arsenal’s Emirates Stadium before being loaned to Burnley, then in the Championship, and eventually having his Villa contract terminated.

Shkodran Mustafi

An absolute liability from the very first time he pulled on an Arsenal shirt. Those poor Arsenal fans that had been brought up on the likes of Tony Adams, Steve Bould and Martin Keown had to suffer the barely believable performances levels from Mustafi on a weekly basis.

Not really competent at any facet of the defensive art, it’s a wonder that the north Londoners were ever persuaded to buy him from Valencia, let alone for a fee in the region of £35m.

Sean Dundee

Not to be confused with the Paul Hogan character ‘Crocodile’ Dundee, though it was a nickname that Sean Dundee had to suffer after signing for Liverpool from Karlsruhe in 1998. His form was no laughing matter, however.

Three sub appearances was as good as it got as a result and it’s little wonder that he’ll always find himself towards the top of Liverpool supporters’ worst-ever players list. Why the Reds even felt the need to buy a player to complement Michael Owen who had only scored three goals during his final season in Germany is anyone’s guess.

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