Chelsea fans celebrated the biggest deal of them all Buffalo Bills Pet Gear in the Todd Boehly era on transfer deadline day as Argentina World Cup star Enzo Fernandez joined from Benfica.Indeed the deal is also the biggest of them all in British football history, with no player having ever commanded a greater fee than the 106.8 million it took to secure Fernandez.The 22-year-old midfielder was Chelsea's eighth signing of the mid-season window, with Ukraine winger Mykhailo Mudryk joining him on the list of most expensive Premier League transfers.However, over recent years, the biggest transfer outlays in the richest league have rarely worked out exactly how all parties might have hoped, as the list below shows.MORE: Benfica have every right to feel bruised by a month-long saga that, until the final few days of trading, looked set to conclude with Fernandez staying put in Lisbon. They can console themselves with the gargantuan fee received for a player who cost them a mere 10m from River Plate last June.Fernandez was already on the radar of major clubs acro s Europe before a starring role in Argentina's World Cup triumph sent him into the stratosphere. As he did in the opening defeat to Saudi Arabia, Fernandez came off the bench to score a sumptuous game-sealing goal in the nervy 2-0 win over Mexico and was then a mainstay on the road to glory.Graham Potter will hope he has a similarly transformative effect upon a Chelsea side that has been overdue a midfield refit, although the fact the World Cup final win over France was only his 10th senior cap underlines how much this outlay on an obviously gifted player is a bit of a punt.Coming soon. Chelsea FC (@ChelseaFC) Cody Ford Jersey Grealish headed the opening goal in last month, taking him to four goal involvements in the past three Premier League away games despite a tricky spell for Pep Guardiola's side. The England international could do with this being the start of a purple patch, given he has only scored five top-flight goals in 18 months with the reigning champions.The particular tactical requirements given to Grealish at City act in mitigation, to an extent, but his only three Premier League a sists this term have come in the past month. The United game was the latest in a succe sion of high-profile games where the former Aston Villa hero has found himself among the substitutes. That alone is a situation that has to change if he is to prove to be value for a considerable sum of money.Jack Grealish scores off the bench to give Man City a derby lead! What a time to bag his second of the season! Football on BT Sport (@btsportfootball) Jack Grealish didnt need long to score after coming on.How about that KDB a sist, though?! :drooling_face::film_camera: via CBS Sports Golazo :football2: (@CBSSportsGolazo) Fresh from their surprise run to Champions League glory under Thomas Tuchel, Lukaku was supposed to be the final piece in the puzzle for Chelsea. As it happened, his arrival simply picked the puzzle up, shook the box around vigorously and chucked it out of the window. After firing Inter to Serie A glory, Lukaku could only manage eight Premier League goals in 26 games and never appeared to be an easy fit for Tuchel's system, given Chelsea had found succe s with a mobile and interchangeable front three in the first half of 2021. A year after his signing, Lukaku was back at Inter and Tuchel was about to be sacked. The transfer that was supposed to herald a return of the glory days to Manchester United eventually came to symbolise their decline in the post-Alex Ferguson years. Pogba arrived in the same summer Jose Mourinho took the reins and that dream team would prove to be a toxic marriage.It should be noted that when United played their best football during recent seasons, Pogba was often e sential, most notably when they finished second in the Premier League under Ole Gunnar Solskjaer in 2020/21. However, none of Mourinho, Solskjaer or Ralf Rangnick could find a way to consistently Cam Lewis Jersey prompt his best form and Pogba's woes generally coincided with long collective slumps and embarra sing defeats. After six largely unhappy years, he joined Juventus on a free transfer from United for the second time in his career.Pogback! Thank you Manchester!! Paul Pogba (@paulpogba) Lukaku's second appearance on this list isn't much more pleasant. Everton received an initial 75m, with 15m more in add-ons and an ageing Wayne Rooney thrown in the bargain.Pogba and Zlatan Ibrahimovic were the stars Von Miller T Shirts as United won the EFL Cup and Europa League while finishing sixth in the league in Mourinho's first season.It was hoped Lukaku would elevate them into the title picture but their eventual second-placed finish was 19 points behind Manchester City's record haul of 100. Mourinho's demise midway through the following campaign brought Solskjaer to the club and a master finisher from his playing days decided Lukaku did not figure in his plans. A return of 28 goals in 55 Premier League appearances was not appalling but few mourned his departure. Any list like this nowadays delves into the vagaries of up-front fees, instalments and add-ons. Chelsea agreed an initial fee of 72m for Havertz, with two further chunks of 9m depending on appearances and honours won. The Germany international accounted for a decent chunk of those additional payments when he scored the only goal in the 2021 Champions League final against Manchester City.It speaks of a curious Chelsea career so far that such an act, which prompted further silverware in the UEFA Super Cup and Club World Cup, has not made Havertz a Stamford Bridge hero. By default, he has played the majority of his football at centre-forward for a team lacking strikers, which still does not feel like a natural fit. The formidable, free-scoring attacking midfielder of Havertz's Leverkusen days has only been seen fleetingly.:large_blue_circle: Key moment in the final as Mason Mount sets up Kai Havertz :football2:@masonmount_10 | | UEFA Champions League (@ChampionsLeague) Some of the transfers on the list represent presumed sure things that proved to be nothing of the sort; the lack of any apparent guarantees in Mudryk's transfer is one of the factors that makes it so intriguing.He scored seven goals in 12 Ukrainian Premier League games this term and three in six Champions League group outings underlined his abundant talent. But he leaves Shakhtar making a club he appeared fewer than 50 times for an awful lot richer. Mudryk does not have a foundation of senior experience to fall back on as he tries to make his way at a club in flux that already has a frankly ludicrous number of wide attacking options.MORE: Insofar as there's any discernible plan in Chelsea's transfer busine s at the Ed Oliver Jersey moment, Mudryk represents an investment in the future. The same can be said for Brazil international Antony, who cost United a little over 1m for each of his 82 Ajax appea