Ronaldo ‘approves transfer’ with Man City ahead of Premier League return

The clock is ticking until the last few days of the summer transfer window and there will likely be a late rush to close deals before it closes. Premier League clubs have until 11pm on August 31st to do their business and dust off, with some transfers going straight on the wire over the years.

Due to the rapidly changing nature of the transfer window, some clubs often take the risk of a last minute deal.

Occasionally, they can pay off well. Liverpool signed Luis Suarez on the January 2011 deadline, while a young Wayne Rooney was acquired by Manchester United in 2004.

But there is no denying that clubs are just as capable of making horrific mistakes, and so are the players who are looking for their perfect game.

Injuries can do their part as the Premier League season has already started and the third week of play of the season takes place just before the window closes.

That could lead some teams to make knee-jerk decisions to reinforce their roster until the market reopens in January.

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Andy Carroll and Danny Drinkwater: The pair were an expensive flop for Liverpool and Chelsea (Image: Express Sport)

Looking back on past deadline days, there are certainly transfers that didn’t work out – and Express Sport picks five of the most regrettable deals …

Danny Drinkwater

Chelsea had spent most of the transfer window signing Radja Nainggolan as part of Antonio Conte’s plans to build on his 2016-17 title win.

And the Italian’s replacement plan called for him to replace Leicester midfielder Danny Drinkwater, who had played a key role in the Foxes’ shock title triumph a year earlier.

Drinkwater had been Jamie Vardy’s supplier several times in that title-winning campaign, and the £ 35 million fee at the time reflected his notoriety in English football.

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The midfielder played a prominent role in Conte’s first season, playing 43 games in his first season at Stamford Bridge.

But he soon fell out of favor after trying to make an impact, and problems off the field soon tarnished his future with the blues.

He has been loaned out to Aston Villa, Burnley and Turkish club Kasimpasa and the club will be firing him this summer.

At 31, Drinkwater may be wondering what his prime years in Leicester would have been like.

Danny Drinkwater: Chelsea midfielder has not been with us since 2018 (Image: Getty Images)

Andy Carroll

The formidable striker had everything he wanted at his youth club, Newcastle United.

Carroll had graduated from the club’s academy and became a first-team regular in the 2009-10 season.

But it was the following year that he scored 14 league goals before December and convinced Kenny Dalglish to spend a club record of £ 35million on Carroll.

It seemed like a sensible way to spend the proceeds of the Fernando Torres sale, but the Englishman struggled to transfer his form from Tyneside to Merseyside.

Andy Carroll: The £ 35 million new signing fought for goals in Liverpool

Andy Carroll: The £ 35 million new signing fought for goals in Liverpool (Image: Getty Images / Liverpool FC)

Injuries hampered his progress and he was constantly left out under Brendan Rodgers when he replaced Dalglish in 2012.

After just 11 goals in 58 games, Carroll left to join West Ham on a £ 15m deal before returning to St James’ Park in 2019.

Now, a free agent, few could blame Carroll for taking the plunge. But how many goals would have been scored if he had stayed in familiar surroundings?

Peter Odemwingie

One of the most famous Deadline Day stories of all time was West Brom striker Peter Odemwingie showing up outside in the parking lot in front of QPR’s training ground to get a 2013 move through.

Peter Odemwingie: The move from West Brom's striker to QPR has failed

Peter Odemwingie: The move from West Brom’s striker to QPR has failed (Image: Getty Images)

Oddly enough, there seemed to be a misunderstanding and the two clubs had yet to agree on a deal for the Nigerian, only accepting his part of an exchange deal with Junior Hoilett.

“Everything seemed agreed, but actually I didn’t know one of the terms was that she [West Brom] got hoilett and [if I had known that] I would never have gone to London, “Odemwingie told Transfer Talk.

“Why would I have gone to London in bad weather? It was already dark, it was winter and I had just had a newborn baby that was a week old.

“I would have done one thing [if I had known] Call my friends at QPR and say, ‘Hey guys, can you find out if Hoilett is actually coming to West Brom or not?’ “

Eventually Odemwingie stayed with the Hawthorns, but only for another five months and was disciplined for his part in the transfer chaos.

He eventually joined Cardiff on a £ 2.25 million deal but struggled to reach the heights he’d reached in the Midlands.

Thomas Partey

It was seen as a coup when Arsenal signed Thomas Partey from Atletico Madrid and paid his £ 45million release clause in full.

But after his first full season at the Emirates Stadium, the Ghanaian must have some doubts whether he made the right decision.

Thomas Partey: Arsenal paid £ 45m to sign Thomas Partey from Atletico Madrid

Thomas Partey: Arsenal paid £ 45m to sign Thomas Partey from Atletico Madrid (Image: Getty Images)

The Gunners had ambitions to get back into the Champions League qualifying spots but instead began with their worst start to a Premier League season.

Partey has had some frustrating times on the sideline due to his injury issues and only made 24 league games last season.

Back in Madrid, Diego Simeone’s side had better times when Atletico won the title for the first time since 2013-14.

The 28-year-old also missed a winners medal this year after loaning out the season at Real Mallorca – and will no doubt be scared of missing him again as Arsenal continue to struggle.

Kostas Mitroglu

Fulham was taken over by Shahid Khan in 2014 and with a new manager on the hot seat in Felix Magath, transfers kept coming back as Fulham tried to avoid relegation.

Kostas Mitroglu: Mitroglu only played three games for Fulham at PSV Eindhoven

Kostas Mitroglu: Mitroglu only played three games for Fulham at PSV Eindhoven (Image: NurPhoto)

Switching to Kostas Mitroglu seemed a breeze given the striker’s excellent record at Olympiacos, but it also begged the question of why no other clubs were there for him.

Mitroglou had established himself as the clinical finisher with 81 goals in 182 games for the Greek giant.

The cottagers paid £ 12 million to bring Mitrolgu to Craven Cottage on the January 2014 deadline.

However, due to injury problems and poor form in the relegation of Fulham to the championship, he was only used three times for the West London team.

In August 2014 he was loaned to Olympiacos again, where he rediscovered his scoring chances and later moved to Benfica.

But his detour through the English capital is certainly a step in his career that he would like to forget.