Summer Transfer Window – The Premier League’s Winners and Losers

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The proverbial Premier League transfer window has slammed shut. As of 11 pm on Monday 5th October, top-flight clubs in England can no longer do business outside these shores. The domestic window remains open until 16th October, allowing English clubs to do business with one another although the majority of the main deals have already taken place. Let’s take a look who came out on top and who should have done better.

The Premier League’s Winners and Losers of the Summer Window

Transfer Window Winners


Hindsight is a wonderful thing, but there’s a reason why Carlo Ancelotti’s Everton sit pretty at the top of the table going into the first international break of the season.

The Italian has totally overhauled Everton’s midfield, so much so that an argument could be made that Ancelotti has the best midfield trio in the Premier League. The acquisitions of James Rodriguez, Allan and Abdoulaye Doucoure have transformed the Toffees fortunes this campaign, making it four wins in as many matches in the league.

They have also added defensive solidity with the signing of Ben Godfrey from Norwich City.

Going the other way is Moise Kean (PSG) and Theo Walcott (Southampton) on season-long loans while Morgan Schniederlin sees his disappointing time at Goodison come to an end, joining French side Nice on a permanent transfer.


After guiding Chelsea into the Champions League spots last season, Frank Lampard wasted no time in improving his squad for the 2020/21 campaign. Timo Werner (RB Leipzig) and Hakim Ziyech (Ajax) were brought in early on, while Ben Chilwell (Leicester City), Malang Sarr (Free), Thiago Silva (Free), Kai Havertz (Bayer Leverkusen) and Edouard Mendy (Rennes) take Chelsea’s spending spree north of £200 million. 

Lampard now has an embarrassment of riches at his disposal, which could also be his undoing. Surely a squad of that quality and depth should be bettering last seasons fourth-placed finish.

Tottenham Hotspur

The decision to bring Gareth Bale back to Spurs on loan from Real Madrid will obviously catch the headlines but it’s the clever additions of Matt Doherty from Wolves and Sergio Reguilon from Sevilla that are key. Spurs now have two assured pairs of full-backs to alternate between, the aforementioned Doherty and Reguilon as well as Serge Aurier and Ben Davies.

Pierre-Emile Hojbjerg has been brought in from fellow Premier League side Southampton to add solidity to the midfield, and it seems to have paid dividends already as the Dane impressed in Tottenham’s 6-1 demolition of Manchester United at the weekend. The only downside for Jose Mourinho was the inability to bring in a central defender. Inter Milan’s Milan Skriniar was heavily linked throughout the window, however, remained in Italy.

Aston Villa 

Villa’s best bit of business this window wasn’t an incoming transfer, it was luring Jack Grealish away from potential suitors after tying the Villa captain down with a new and improved five-year deal. Grealish had been heavily linked with a move away from Villa Park, with Manchester United the likely destination, but the England international stayed true to his boyhood club.

Elsewhere, Dean Smith dipped into the Championship for Matty Cash (Nottingham Forest) & Ollie Watkins (Brentford), with the latter breaking Villa’s transfer record. There was an upgrade in goal too, as Arsenal’s Emiliano Martinez joined on a permanent deal while Ross Barkley, somewhat surprisingly, opted for a season-long loan deal from Chelsea. 


The Gunners, much like Aston Villa, managed to keep hold of their most prized possession during the summer transfer window – Pierre-Emerick Aubameyang. Arsenal’s main man penned a new deal, keeping him at the Emirates for the immediate future after weeks of teasing on social media. There was deadline drama in North London too as Thomas Partey finally joined last season’s FA Cup winners, after seemingly years of speculation. In addition, Willian swapped blue for red as the Brazilian opted to join Arsenal after his contract came to an end at Stamford Bridge.

Mikel Arteta also reinforced his backline with signing Gabriel from Lille and making Pablo Mari’s loan from last season a permanent move. In the other direction, Henrikh Mkhitaryan moved to Roma and Emiliano Martinez – who impressed towards the back end of last season – decided to join Aston Villa instead of playing second fiddle to Bernd Leno as Arsenal’s number one.

Transfer Window Losers

Manchester United

Where to start? Manchester United’s summer-long pursuit of Borussia Dortmund winger Jadon Sancho ended without a pay-off. The 6-1 thrashing by Tottenham Hotspur on the penultimate day of the window left fans with more questions than answers, especially going into the final day with only one summer addition – Donny van de Beek – who is yet to start a Premier League game. Barcelona winger Ousmane Dembele was briefly touted as an alternative to Sancho however, like many other deals during this window, it fell through.

A quadruple of arrivals joined on deadline day, 33-year-old striker (and free agent) Edinson Cavani and left-back Alex Telles from FC Porto along with youngsters Facundo Pellistri and Amad Traore – with the latter joining on 1st January 2021. Instead of bringing in a well-needed centre back, Chris Smalling left on a permanent deal, joining Roma where he spent last season on loan. Among the doom and gloom, there was one positive with Alexis Sanchez ending his Old Trafford nightmare, leaving for Inter Milan. 


There were times post lockdown where Burnley boss Sean Dyche couldn’t name a full matchday squad, naming two goalkeepers on the bench against Manchester City. So surely reinforcements were necessary heading into the 2020/21 campaign. Although, that hasn’t been the case. Third choice keeper Will Norris and 31-year-old Dale Stephens from Brighton & Hove Albion hardly screams a successful transfer window. They did, however, manage to steer James Tarkowski away from the advances of West Ham, so that’s something, right?

West Ham United

Speaking of West Ham, the Hammers haven’t had the best of windows either. Despite impressive league victories over Wolverhampton Wanderers and Leicester City, West Ham fans have had nothing to get excited about. If anything they’ve been left angry – just like club captain Mark Noble. The midfielder didn’t hide his displeasure when promising youngster Grady Diangana was sold to West Bromwich Albion to raise transfer funds – tweeting his disapproval.  

The only incoming transfers for the first team were Slavia Prague duo Vladimir Coufal and Tomas Soucek – with the latter making a permanent move to the London Stadium following a decent loan spell last season.

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