Two Arsenal players feature in the best Premier League buy in each of the last 20 windows

With the transfer market back open, we have picked the best signing made by a Premier League club in the last 20 windows, starting with a Jose Mourinho favourite…

The worst of every window are here…

Winter, 2014 – Nemanja Matic (Benfica to Chelsea, £21m)
Chelsea were busy boys in January 2014, and are busy in this list, occupying the winning slot in the first two windows. The Blues signed Bertrand Traore, Kurt Zouma, Mohamed Salah and Matic, while offloading Juan Mata to Man Utd and Kevin De Bruyne to Wolfsburg.

Matic instantly became a mainstay in the starting XI, being named in the PFA Team of the Year in 2015 as Chelsea won the Premier League.

The Serbian defensive midfielder was sold to Man Utd for around £40m in 2017, being reunited with Jose Mourinho. Chelsea got the best three years of Matic’s career before doubling their money for him. What a transfer.

Summer, 2014 – Diego Costa (Atletico Madrid to Chelsea, £32m)
What a window this was. Alexis Sanchez joined Arsenal, Southampton signed Sadio Mane and Hull brought Andy Robertson to England for only £2m. Yet, we have opted for another Chelsea player.

It was a tough choice between Cesc Fabregas and Costa, giving the edge to the striker as he epitomised what that Chelsea side were all about. Costa also had to adapt to the league, which he did straight away. Fabregas had been there before with Arsenal and was world-class at the Blues’ London rivals.

Costa bagged 20 Premier League goals in 26 matches during his maiden season in England as Chelsea won the title. Atletico re-signed the Spanish striker for a rumoured £57m in 2018. Prime years and profit again? Hats off.

Winter, 2015 – Wilfried Zaha (Man Utd to Crystal Palace, £3m)
The debate of who was the better transfer out of Dele Alli to Tottenham for £5m or Wilfried Zaha returning to Crystal Palace for £3m was one we didn’t know we needed; it was very difficult to pick a winner.

Alli became one of the best players in the country almost immediately, going to Euro 2016 and the World Cup in 2018 as well as being named the Young Player of the Year in 2016 and 2017. He has drastically fallen off in recent seasons, which is pretty sad to see.

Zaha, on the other hand, just takes it ahead of Alli due to his consistency, and the fact that Crystal Palace would probably be in the Championship if it wasn’t for him.

He re-joined the Eagles having struggled for game time at Man Utd and has more goals and more assists than any other Palace player in Premier League history.

Summer, 2015 – N’Golo Kante (Caen to Leicester, £5.6m)
Kante came to England an unknown quantity, only to become (arguably) the most important player in the most extraordinary league title win in football history.

The French defensive midfielder was an absolute hit at the King Power and after his excellent 2015/16 campaign, moved to Chelsea. He won another league title in his debut season, as well as being named PFA Player of the Year.

It is worth mentioning that in this summer Man City signed Kevin De Bruyne and Raheem Sterling, Southampton purchased Virgil van Dijk and Tottenham bought Son Heung-min. And it wasn’t even slightly close to being a debate for who the best signing was.

Winter, 2016 – James Maddison (Coventry to Norwich, £2.3m)
We know what you’re thinking, but no, Steven Caulker’s loan to Liverpool does not make top spot for the best transfer in January 2016. But as you can probably guess, this was not the most star-studded window of all time.

Maddison was signed for pennies and sold on for a £22m profit. He has obviously played his best football for Leicester and Tottenham, but kudos to the Norwich scouting department.

Summer, 2016 – Sadio Mane (Southampton to Liverpool, £34m)
Kante’s £32m move to Chelsea has narrowly missed out here. Also in the summer of 2016, Ilkay Gundogan joined Man City for £21m and Zlatan Ibrahimovic moved to a Premier League club for the first time in his career, signing for Man Utd as a free agent and helping them win the League Cup and Europa League.

As for Mane, he was world-class at Anfield since day one and was the first brilliant piece of business Jurgen Klopp produced on Merseyside.

Mane scored 120 goals for the Reds, including one in a Champions League final defeat to Real Madrid and was superb as Liverpool won their first Premier League crown in 2020, netting 18 times in 35 games.

Mane, Mohamed Salah and Roberto Firmino blossomed into one of the finest frontlines in English football history. The Senegal forward was the first of the famous three to leave Anfield, joining Bayern Munich in 2022.

Winter, 2017 – Wilfred Ndidi (Genk to Leicester, £15m)
The Foxes tried to replace Kante – an impossible task – by signing Nampalys Mendy from Nice, which never quite worked out. Ndidi was the closest they came to filling the void left by the 2018 World Cup winner.

In a straight battle between Gabriel Jesus to Man City, the Nigerian midfielder was the best deal of January 2017 due to his consistency, transfer fee, superb ability and sell-on potential (which was never exercised).

Summer, 2017 – Mohamed Salah (Roma to Liverpool, £37m)
Another very strong window, but another very easy decision. Salah was the first of Liverpool’s big three to get them over the Champions League and Premier League hump. You’ll know the other members of said big three soon, if you don’t already.

The Egyptian beats the likes of Ederson, Bernardo Silva, Andy Robertson and Antonio Rudiger here.

Winter, 2018 – Virgil van Dijk (Southampton to Liverpool, £75m)
Liverpool were chasing van Dijk for an eternity before eventually getting their man, spending a monumental amount of money to push the deal over the line.

The Netherlands defender has been one of the most important players for any top-flight side in Premier League history. His presence made teams fear Liverpool again, and he helped the Reds reach the Champions League final in his first season, despite joining halfway through.

Klopp’s side would previously drop silly points against relegation fodder, but that was no more after Van Dijk joined; he sorted the shaky defence out seamlessly. £75m ended up being, dare we say, an absolute bargain. They had one last position to sort out before the Klopp jigsaw was complete…

Summer, 2018 – Alisson (Roma to Liverpool, £65m)
…and complete it was. £65m was a lot to spend on a goalkeeper, but just like Van Dijk, Alisson was absolutely worth it.

This was a difficult window to find a definitive answer for, though. Brighton also bought Yves Bissouma, Man City brought in Leicester legend Riyad Mahrez, the Foxes replaced him with James Maddison and Chelsea signed the apparent third-best player in the world in 2021, Jorginho.

Alisson addressed a position that desperately needed a permanent fix, coming in and having the same fear-factor impact as Van Dijk. The Reds became European champions in Alisson’s maiden season in England, and Premier League winners a year later.

The 31-year-old’s best moment for Liverpool was scoring a goal to secure them a top-four finish. What a moment.

Winter, 2019 – Youri Tielemans (Monaco to Leicester, loan)
Tielemans joined Leicester on loan, making his move to the King Power permanent in the summer. If it wasn’t for the loan, Leicester would probably not have paid £32m for the Belgian. His winning goal in the 2021 FA Cup final wins him this particular accolade all by itself – not to undermine his largely terrific performances in the Premier League.

Summer, 2019 – Gabriel Martinelli (Ituano to Arsenal, £5m)
Martinelli has been far from outstanding this season but there is no doubt that this is the best signing from this transfer window, and Arsenal’s best since Arsene Wenger left the club.

The Brazilian has blossomed into one of the best wingers in the Premier League under Mikel Arteta and enjoyed his best goalscoring season in 2022/23, netting 15 times in the top flight.

Should the Gunners sell Martinelli, they might make a slight profit on the £5m it cost them to bring him over from Brazil.

READ MORE: Saliba 3rd in ranking of every signing made by Arteta and Emery since Wenger left Arsenal

Winter, 2020 – Bruno Fernandes (Sporting Lisbon to Man Utd, £47m)
Man United have made some very questionable signings since the retirement of Sir Alex Ferguson, but Fernandes was a rare piece of good business post-Fergie.

The Portugal star needed no time to settle into life in the Premier League, and didn’t lose a single game in the top flight during his first half-season, scoring eight and assisting seven in 14 matches.

United finished second in Fernandes’ first full season, as he contributed to 29 goals. He slowed down after Cristiano Ronaldo returned to Old Trafford, but at his absolute best, was keeping Ole Gunnar Solskjaer in a job at times.

Summer, 2020 – Thiago Silva (PSG to Chelsea, free)
After initially choosing Raphinha’s £17m move to Leeds, we changed to Thiago Silva, who joined Chelsea for nothing from PSG.

Silva has been brilliant for the Blues and is one of not many excellent signings made by the Londoners in recent years. Aged 38, the former AC Milan captain is still going strong.

READ MORE: Caicedo 12th, Lukaku 50th: Ranking the last 50 signings made by free-spending Chelsea

Winter, 2021 – Moises Caicedo (Independiente to Brighton, £2m)
Jesse Lingard joined West Ham on loan for the second half of 20/21 and was incredible as the Hammers narrowly missed out on the Champions League places.

Caicedo, though, was immense for Brighton after signing for peanuts and then joined Chelsea for what could be a British record fee. What a piece of business.

Joe Willock’s loan to Newcastle is also worth a mention, as his goals played a huge part in the Magpies’ survival in 20/21.

Summer, 2021 –  Martin Odegaard (Real Madrid to Arsenal, £32m)
Arsenal made some stellar signings including Aaron Ramsdale and Benjamin White, but Odegaard was their best and the best of this window. Signed for what has turned out to be a bargain price of £32m, Odegaard has taken the armband and was central to the Gunners’ title push last season.

Gray, Cristian Romero, Marc Cucurella (to Brighton, of course), Michael Olise, Conor Gallagher and Emmanuel Dennis all miss out here. Narrowly.

Winter, 2022 – Bruno Guimaraes (Lyon to Newcastle, £36m)
Christian Eriksen’s move to Brentford was in with a shout. Luis Diaz, Rodrigo Bentancur and Julian Alvarez all deserve a mention. Kieran Trippier was our original choice. But Guimaraes is the one for us.

£36m for the Brazilian midfielder quickly became a steal for Newcastle and it would not be surprising to see him representing the all-white of Real Madrid soon.

Summer, 2022 – Erling Haaland (Borussia Dortmund to Manchester City, £51m)
Looking at other deals in this window wasn’t even necessary, was it?

Winter, 2023 – Anthony Gordon (Everton to Newcastle, £40m)
We are many who have been left surprised by how successful Anthony Gordon has been at St James’ Park. He has quickly proved himself to be a big-game player worth the money Newcastle paid Everton for his signature.

Mario Lemina deserves a shoutout for his solid performances in a Wolves shirt, all for a very modest £9.7m.

OPINION: Newcastle have a gem in Gordon and we have never been so wrong about a player

Summer, 2023 – James Maddison (Leicester to Tottenham, (£40m)
Declan Rice might have been our Premier League signing of the season but that was because of James Maddison’s injury.

Spurs made a few top-class signings last summer, including Pedro Porro, Guglielmo Vicario and Micky van de Ven, but Maddison looks to be the best addition out of the lot, even if we are basing it off a couple of months.

Despite all of those signings and other stars like Heung-min Son, Yves Bissouma and Cristian Romero, any success at the Tottenham Hotspur Stadium will be inspired by Maddison.