The English midfielder arrived at Stamford Bridge in 2017 one year after playing an integral role in Leicester's shock Premier League title triumph, with Antonio Conte and Co forking out £35million to prise him away from the King Power Stadium.
Yet after featuring 22 times in his first season, Drinkwater only made one appearance in his next four years in west London, spending the majority of his time out on loan and encountering a number of problems off the pitch.
Danny Drinkwater's miserable spell at Chelsea is set to end upon the expiry of his contract
The midfielder made just 22 appearances at Stamford Bridge after signing for £35million
Following a loan spell at Reading in the 2021/22 campaign he announced this week that he will be leaving Chelsea for free in the summer, while describing his move to Stamford Bridge as a 'business deal gone wrong'.
And ahead of his departure in July, Sportsmail has taken a look at where Drinkwater's failed transfer to Chelsea ranks amongst the worst in Premier League history.
5. Bebe - Vitoria de Guimaraes to Manchester United (£7.4m)
Sir Alex Ferguson pulled off some masterstrokes in the transfer market over the years, but that's not to say the legendary Manchester United boss didn't have his fair share of stinkers too.
And Bebe, who he brought to Old Trafford for £7.4mfrom Portuguese club Vitoria in 2010, most likely goes down as his worst.
The winger had not played above Portugal's third tier when Ferguson's former assistant Carlos Queiroz made the recommendation to sign him and, just five months after he joined Vitoria, Bebe found himself on his way to Old Trafford.
Drinkwater's move goes down as one of the worst in Premier League history, joining Sir Alex Ferguson's most infamous Manchester United flop, Bebe (left)
Ferguson claimed he had never seen his new recruit play despite approving the deal, which quickly became evident when he produced a string of awful displays in his debut season.
After featuring seven times that year, racking up just 75 minutes worth of Premier League action, Bebe spent the final three seasons of his United career out on loan before leaving to join Benfica for almost £3m.
It may not have been the most financially damaging for the club, yet Bebe's bizarre stint at Old Trafford proved one of Ferguson's greatest blunders.
The player's own comments on the transfer in 2019 really did speak volumes: 'At first I thought it was a joke [when told of United's interest], but then I saw it was true and understood that it was a unique opportunity.'
Bebe only featured seven times for United before he was sold to Benfica for £3m in 2014
4. Danny Drinkwater - Leicester to Chelsea (£35m)
Next up is Drinkwater himself, a player who was at least expected to play a rotational role after completing his expensive move to Chelsea from Leicester in 2017.
Alongside midfield partner N'Golo Kante he helped write a true sporting fairytale by capturing the Premier League with the Foxes, though it's fair to say he never reached similar heights as his old pal in west London.
Antonio Conte used Drinkwater 22 times in the 2017/18 campaign, however the Italian's successor Maurizio Sarri cast the midfielder to one side the next season, only using him in the Community Shield.
It was at the end of this sorry campaign when his Chelsea career and general reputation took a turn for the worst; in April 2019, Drinkwater was charged with drink driving after crashing his Range Rover in Cheshire, injuring two passengers in the process.
The incident sparked a downward spiral in his fortunes and off the pitch. During a loan spell with Burnley in 2019/20, he found himself at the centre of controversy once again when seen headbutting a man in a nightclub after becoming embroiled in a heated dispute with Scunthorpe United's Kgosi Ntlhe.
Drinkwater's five-year stint at Chelsea was a major disappointment on a number of fronts
He spent the majority of his time out on loan and was involved in plenty of scrapes off the field
He then headed out on another loan to Aston Villa in the second half of that season, but that ended in disgrace when a training ground bust-up with Jota resulted in the club terminating his loan.
The crestfallen player then enjoyed a brief stint in Turkey with Kasimpasa, a stint in Chelsea's reserves and a loan spell at Reading last term.
Drinkwater is now set to depart Chelsea in July, marking a truly disastrous £35m purchase for the club.
3. Ricky Alvarez - Inter Milan to Sunderland (£10m)
When Sunderland agreed a £900,000 loan fee with Inter for the Argentina international, which included a £10m obligation-to-buy clause, little did they know he would end up costing them close to £20m and be gone the following summer.
Alvarez's loan had a clause which forced the Black Cats to buy him outright should they stay in the Premier League that season and a problematic left knee didn't prevent him from completing a medical.
He went on to feature 13 times for the club in 2014/15, scoring one goal and just about helping them maintain their top-flight status. Nevertheless, Alvarez was restricted to that number of appearances after injuring his opposite knee, which he had had surgery on years earlier.
Ricky Alvarez's loan move to Sunderland in 2014 eventually cost the club close to £20m
Alvarez left the Black Cats on a free the following summer but they were forced to pay an obliged £10m transfer fee as well as over £5m in compensation
Sunderland then argued that they were not obliged to buy him outright, claiming his right knee problem was a product of his left knee troubles originally acknowledged in the agreement.
As the dispute continued, Alvarez was not offered a new contract at the Stadium Of Light and he was therefore free to join Sampdoria on a free transfer in 2015. And two years later, the Court of Arbitration for Sport ruled that Sunderland were liable to pay the £10m transfer fee in full, rejecting their appeal on the basis they had discovered a problem with his right knee in the medical and chosen not to bring it up with Inter.
If that wasn't bad enough, the Premier League club then lost their claim that Inter should have repaid some of the loan fee and wages as a result of the injury, before Velez Sarfield, Alvarez's former club, successfully sued them for £305,000 in solidarity payments.
On top of that, Alvarez himself then took Sunderland to court in 2019 over his loss of earnings during the period his contract situation was in dispute, and he was eventually awarded £5m in compensation from the club.
In the end, it is believed the Black Cats lost almost £20m on the transfer, which lasted all of 13 appearances and 15 months before he left free of charge. Calamitous.
2. Nicolas Pepe - Lille to Arsenal (£72m)
Unlike the other players in this list, Pepe still has the chance to go on and make his inclusion here look foolish. At the age of 26 his peak years could still be to come.
However, the Ivory Coast winger has so far utterly failed to live up to his mammoth transfer fee since heading to Arsenal in 2019.
There was plenty of hype and expectation around him when he rocked up at the Emirates, having produced a return of 37 goals and 18 assists in 79 appearances for Lille.
So far in north London, though, Pepe is yet to truly live up to his potential and justify his £72m price-tag.
A tally of 27 goals and 21 assists in 112 outings is disappointing, and in the previous season he was only afforded five Premier League starts by Mikel Arteta after falling behind the likes of Bukayo Saka, Gabriel Martinelli and Emile Smith-Rowe in the pecking order.
Reports recently suggested Arsenal are even prepared to cut their losses and offload Pepe, who still has two years to run on his contract, for as little as £35m in the summer transfer window.
If he fails to revive his Gunners career in the future, Pepe's switch to England will go down as one of the most expensive failures in Premier League history.
And to think they could have at that time signed Wilfried Zaha for the same fee but instead opted for Pepe...
Nicolas Pepe's £72m switch to Arsenal is set to go down as a hugely expensive mistake
The Ivory Coast winger has failed to live up to his price-tag and could now depart this summer
1. Angel Di Maria - Real Madrid to Manchester United (£60m)
When assessing the Premier League's highest-profile flops, Di Maria's £60m move to Old Trafford pretty much ticks all boxes: proven world-class player, tick; Champions League winner, tick; massive transfer fee, tick; huge expectation, tick; major disappointment, tick. And then, to top it all off: hugely bitter fallout, tick; and having him come back to bite you in competition, tick.
The Argentinian had registered 36 goals and a staggering 84 assists in 190 appearances for Real Madrid when United came calling in 2014, winning the Spanish title and Champions League in the process. He was also a member of the Argentina side which reached the World Cup final that summer.
His arrival in Manchester initially looked like £60m very well spent when he recorded three goals and four assists in his first six Premier League matches, yet that was as good as it got for him in the Premier League.
Over the next seven months, Di Maria failed to score another league goal for United, with his only other strike coming in an FA Cup tie against minnows Yeovil.
He never replicated the type of form so often displayed in his spell at the Bernabeu, meaning he eventually fell down in Louis van Gaal's pecking order and was reduced mainly to appearances off the bench.
Angel Di Maria arrived at Man United with a reputation as one of the best players in Europe
But his one and only season at Old Trafford went down as a £60m failure for the club
At the end of that miserable campaign United agreed to let Paris Saint-Germain pay £44m to take Di Maria off their hands, however his dramatic revival in the French capital is another indication of how badly things were for him at Old Trafford.
He has since produced 93 goals and 119 assists in 295 outings for PSG, meaning his unfruitful spell in England remains somewhat of a mystery.
Di Maria was even handed United's famous No 7 shirt, previously worn by the likes of Cristiano Ronaldo and David Beckham, in his time at the club. But last year he told TyC Sports: 'I didn't give a f*** about the Manchester United No 7. At first they talked to me a lot about it... it was just a shirt.
'My problem at Manchester was the coach. Van Gaal was the worst of my career. I would score, assist, and the next day he would show me my misplaced passes. He displaced me from one day to the other, he didn't like players being more than him.'
His wife was also unhappy at the club and not shy to let her feelings known.
Speaking to Spanish morning show Los Angeles de la Manana, Jorgelina Cardoso spoke about all the things she hated in Manchester.
'I begged Angel, any place but England,' she said. 'And one year later we were in Manchester, s***.
'I didn't like anything at all. The people were all skinny, neat, weird. You are walking and you don't know if they are going to kill you or not.
'The food is disgusting. The girls all use a lot of make up, like they are dolls.'
Di Maria's wife Jorgelina Cardoso was scathing of Manchester, its food, fashion and women
Di Maria's house was targeted in an attempted robbery in 2015, where burglars are believed to have used scaffolding poles to smash their way into their house.
After this, the family stayed briefly in the Lowry Hotel, and the house was eventually put up for sale when Cardoso was scared to return home.
Di Maria himself cannot even stand the sight of United, according to his former PSG team-mate Marcin Bulka.
'Di Maria hates Manchester United,' Bulka told Polish YouTube channel Foot Truck. 'He has no good memory of the time he spent there.
'In fact, when something related to Manchester United appears on television, he changes the channel quickly.'
Di Maria's return to Old Trafford with PSG in the Champions League in February 2019 highlighted the animosity.
He was bundled into the advertising hoardings by his former team-mate Ashley Young, much to the delight of the unsympathetic home crowd.
Di Maria received a constant barrage of abuse, although he went on to set up both goals in a 2-0 win for his side.
Videos also appeared to show Di Maria telling United fans to 'f*** off' after setting up Presnel Kimpembe to score the opening goal.
A bottle of beer was even launched at Di Maria as he took a corner.
In response, Di Maria taunted the crowd by picking up the bottle before pretending to drink it – an action that UEFA came close to punishing him for.
Yet another case of money well spent by Ed Woodward then. Or maybe not...
Di Maria baited United fans by pretending to drink from a bottle of beer they threw at him
He had the last laugh over the boo boys as he inspired PSG to victory on his Old Trafford return
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