The Premier League transfer window provides some of the most exciting times you can have as a football fan – so much so that it’s almost as entertaining as the actual football season.
Top flight clubs have splashed out more and more as the decades have gone by and it’s a real opportunity for teams to show their ambition and make a statement, though not all business has been successful as players struggle to justify their gargantuan fees.
The likes of Arsenal, Chelsea, Manchester City, Manchester United and Liverpool have dominated the recent transfer windows but there are some that will live long in the memory for supporters after doing some sensational business that had a real impact.
Squawka has taken a look through the history books to assess which are the top ten best Premier League transfer windows of all time.
10. Arsenal (2001/02)
Notable signings: Giovanni van Bronckhorst, Edu, Kolo Toure, Sol Campbell.
Arsenal aren’t really one of those clubs that will look to build a new team in one window, and the late 1990s and early 2000s are prime example of that with the likes of Dennis Bergkamp, Thierry Henry, Emmanuel Petit and Marc Overmars all being brought in over various campaigns.
But in 2001/02, the final season before fixed transfer windows would come in, the Gunners put the finishing touches on the squad they had been building with big signings. The biggest name at the time was Giovanni van Bronckhorst, signed from Rangers, but no player had a bigger impact than Sol Campbell who joined for free from rivals Tottenham.
Also signing Edu and Kolo Toure, Arsenal won the Premier League and FA Cup double that season, but the impact of the transfer window was slightly more lasting. Both Toure and Campbell were part of the Arsenal team that looked to dominate England, winning the Premier League without losing in 2003/04 as well as two more FA Cups. This is only as low as it is because the bigger business had been smartly scattered over previous years.
9. Arsenal (Summer 2025/26)
Notable signings: Viktor Gyokeres, Martin Zubimendi, Piero Hincapie, Noni Madueke, Christian Norgaard, Eberechi Eze
The Gunners get a second place on the list on the sole basis that they have upgraded in every single area on the pitch and brought in players that could make them title winners in the years to come. Whether they do that or not remains to be seen, but this has to be a 10/10 transfer window on paper and one that gives Arsenal their best ever chance of competing with the elite.
Arsenal were crying out for a reliable centre forward. They got it with Viktor Gyokeres, spending £63m in the process. They needed a midfield general who could help Arsenal dominate games alongside Declan Rice. They got it with Martin Zubimendi.
They needed more quality on the wings and someone who could compete with Martin Odegaard in the No 10. In came Noni Madueke and Eberechi Eze. Brentford captain Christian Norgaard also arrived to give the team more steel in midfield.
In defence, Arsenal required a top quality defender who would provide serious competition for Gabriel and William Saliba. In came Piero Hincapie from Bayer Leverkusen. You cannot critique this window and if Arsenal go on to win the title in the years to come, this entry could fly up the rankings.
8. Manchester United (Summer 2007/08)
Notable signings: Nani, Owen Hargreaves, Carlos Tevez (loan), Anderson, Tomas Kuszczak, Rafael
Another window that solidified Manchester United’s place as the dominant force of English football. The signing of Tevez didn’t last long – having actually signed him on a two-year loan – but it had a real impact in helping United win the league.
Tevez scored 14 Premier League goals in the 2007-08 season and 19 in all competitions as he formed part of a dangerous attacking force that included Wayne Rooney, Cristiano Ronaldo and Louis Saha.
Hargreaves was also a quality arrival from Bayern Munich and added experience and quality, despite his struggles to remain fit during his time at United. He still managed to play 34 games that season before his fitness issues emerged.
The arrival of Nani was also a solid one for the club as he went on to play 230 times for the Red Devils, scoring 40 goals and helping the team win four Premier League titles, one Champions League and two League Cups.
Anderson will have a fond place in the hearts of United fans too. The Brazilian may not have been a regular starter for the team, but he did arrive at a time when Paul Scholes, Ryan Giggs and Michael Carrick were thriving under Sir Alex Ferguson and he still played his part with 181 appearances.
The arrivals of Tomas Kuszczak and defender Rafael also provided United with some solid depth to add to their existing talent.
7. Chelsea (Summer 2014/15)
Notable signings: Diego Costa, Cesc Fabregas, Filipe Luis, Loic Remy, Didier Drogba.
The second coming of Jose Mourinho at Chelsea brought a big summer transfer window in 2014/15, with Diego Costa and Cesc Fabregas making their way to Stamford Bridge alongside Filipe Luis, Loic Remy and Didier Drogba.
Although Luis and Remy did not have the impact they would have liked, and Drogba was signed more for his experience, Costa and Fabregas changed the game for Chelsea. A team that had looked toothless in May 2014 was cutting through opposition defences by August, largely thanks to the partnership between Costa and Fabregas. Costa scored 20 goals and Fabregas recorded 18 assists as the Blues won the Premier League at a canter. The duo would combine again for another title in 2017 under Antonio Conte.
What stops them from being higher are a few things. Firstly, the Blues had been silently building over the previous years with Eden Hazard, Oscar and Cesar Azpilicueta already at Stamford Bridge. Costa’s impact was often reserved for the first half of the season, scoring the majority of his goals before Christmas. And then there was the nightmare 2015/16 campaign. It was all just a bit too short-lived.
6. Liverpool (Summer 2018/19)
Notable signings: Alisson, Naby Keita, Fabinho, Xherdan Shaqiri
The Reds used the summer 2018 slot to put some big finishing touches on their squad. Having just lost the 2018 Champions League final to Real Madrid, with a lot of negative attention being placed on Loris Karius, Liverpool brought Alisson in from Roma to become the new number one. Fabinho and Xherdan Shaqiri also signed, while Naby Keita joined with a deal being agreed the previous year.
The impact was almost immediate. Liverpool lost just one Premier League and missed out on the title by a point, but they did claim their sixth Champions League trophy thanks to a 2-0 win over Tottenham Hotspur. Then, a year later, Liverpool had one of the most dominating title wins in Premier League history, essentially wrapping up the league by the start of March – though it wasn’t confirmed until July – with Alisson and Fabinho key.
A large part of Liverpool’s title-winning squad having been signed in the windows before, including Virgil van Dijk in January 2018 and Mohamed Salah in the summer of 2017, is what is currently keeping the Reds in sixth place.
5. Manchester City (Summer 2015/16)
Notable signings: Kevin De Bruyne, Raheem Sterling, Nicolas Otamendi, Fabian Delph
In the summer of 2015, Manchester City were left somewhat licking their wounds having finished eight points behind Premier League winners Chelsea. The Citizens had previously won the league in 2012 and 2014, so were looking to get back to winning ways with the signings of Kevin De Bruyne, Raheem Sterling, Nicolas Otamendi and Fabian Delph.
The immediate result was bad, with City finishing fourth and only securing a place in the Champions League on goal difference. But once Pep Guardiola came in the following summer, the quartet signed in 2015 all shone. De Bruyne is now the best player in the Premier League and an assist fiend, while Sterling has added goals to his game, often proving a frightening opponent in front of goal. The pair, alongside Otamendi and Delph – who found a spot at left-back under Guardiola – helped City win back-to-back Premier League titles, recording 198 points across the 2017/18 and 2018/19 campaigns.
But the fact they needed more signings and a new manager to get to that success, is what slightly holds the window of 2015/16 back.
4. Leicester City (Summer 2015/16)
Notable signings: Shinji Okazaki, N’Golo Kante, Gokhan Inler, Robert Huth, Christian Fuchs.
No big money signings, relatively unknown names brought in, but what a transfer window Leicester City had in the summer of 2015/16. Leicester’s aim in the window would have been to add to a squad that had narrowly avoided relegation, looking to make safety a bit easier to achieve the following campaign. What happened, was remarkable.
Okazaki, Kante, Huth and Fuchs were all absolutely vital to Leicester shocking everyone in football – and even those who don’t care about it – by winning the 2015/16 Premier League title. Kante was understatedly excellent, playing 37 games of the season, Huth played 35, Fuchs 32 and Okazaki 36, scoring five goals. That Kante won the Premier League the following season after joining Chelsea was telling as how much of a gem Leicester unearthed.
The only thing keeping Leicester from arguably having the best transfer window in Premier League history is a lack of longevity (in part due to their best players being tempted away).
3. Manchester City (Summer 2010/11)
Notable signings: Yaya Toure, Mario Balotelli, David Silva, Aleksandar Kolarov, Jerome Boateng.
People will perhaps point to the 2011/12 season for Man City, with Sergio Aguero signing and the Premier League title arriving at the Etihad. But this was Man City’s window. Just look at those names. Yaya Toure and David Silva, who have both gone down as two of the best players in the club’s history, the latter earning himself a statue outside the Etihad.
But let’s not do Mario Balotelli a disservice. There is no Aguero moment without the Italian, who recorded his only Premier League assist in setting up the title win. Or Aleksandar Kolarov, remembered fondly for bombing down the flank with his rocket of a left foot, attacking more than some of the wingers in his team.
Toure, Silva and Kolarov all remained for the 2014 title win and laid down the foundations for Man City’s growth.
2. Liverpool (Summer 2025-26)
Notable signings: Alexander Isak, Florian Wirtz, Jeremie Frimpong, Milos Kerkez, Hugo Ekitike
It’s probably too early to crown them champions of the transfer window considering none of these players have had a full season in a Liverpool shirt yet.
But just based on being bold, splashing whatever cash necessary and getting in ready-made, high profile players who can be game changers on the day, Liverpool score massive points here and soar up the rankings, securing their second spot in the top ten.
And to think Liverpool’s window could have been even better had their move for Marc Guehi not collapsed on deadline day.
Supporters will still be absolutely over the moon with the incredible work Liverpool chiefs did, especially in upgrading their forward line by selling Luis Diaz and Darwin Nunez, then bringing in Hugo Ekitike and Alexander Isak – the later arriving for a British transfer record of £125m.
Liverpool were also quick to upgrade their defensive options after Trent Alexander-Arnold’s departure to Real Madrid, with Jeremie Frimpong brought in to replace him. On the opposite flank, they spent £50m to sign Milos Kerkez, with Andy Robertson now past his peak.
1. Chelsea (Summer 2004/05)
Notable signings: Didier Drogba, Ricardo Carvalho, Paulo Ferreira, Arjen Robben, Tiago, Petr Cech, Mateja Kezman.
The benchmark, however, remains Chelsea’s transformative summer of 2004. The changes may have started in 2003 with the takeover by Abramovich and some important signings being made, but the following year was on a completely different level.
Backed by Abramovich, Chelsea spent big on Didier Drogba, Ricardo Carvalho, Paulo Ferreira, Arjen Robben, Tiago and Petr Cech – though the deal for the latter was technically agreed before the summer. These were statement signings, showing Chelsea meant business, and it paid off. Their first season at Chelsea ended in success with the Premier League and League Cup, followed by another league title.
As the years went on, some players left, including Robben, Tiago and Mateja Kezman but the rest remained for two more FA Cups and a Premier League – including the Double. Then Drogba, Cech and Ferreira were all part of the Chelsea squad that won the Champions League in 2012, with the former two becoming the heroes of the night – almost eight years after initially moving to west London.
There has not been a more important, or better, transfer window by a single club in Premier League history and it will take some beating.
Honourable mentions: Newcastle (1995/96), Manchester United (1998/99), Portsmouth (Summer 2007/08), Southampton (Summer 2014/15), Wolverhampton Wanderers (Summer 2018/19)