Biggest Deadline Day Deals In Recent Times Ahead Of Transfer Window Slamming Shut On Friday

Deadline Day Signings
Deadline Day Signings

The summer transfer window shuts on Friday evening, so ahead of what is set to be an exciting day, we’re taking a look at some of the biggest deadline day signings in the last ten years involving Premier League sides. 

Biggest Deadline Day Deals Involving Premier League Sides

Mesut Ozil – Real Madrid to Arsenal – 2013

Almost ten years to the day, Mesut Ozil joined Arsenal from Real Madrid on a five-year-deal with the Gunners paying around £42.5m for his services, which back in 2013 was a lot of money for a footballer.

His Arsenal career may have ended poorly after he left on a free transfer to Fenerbache in 2021, but Ozil is still one of the most creative number 10s we have seen in the Premier League in recent times.

Ozil achieved a lot during his time at the Emirates with one of his biggest achievements coming at the 2014 World Cup, when Germany were crowned champions. However, he still had a bit of silverware in North London, and was part of three FA Cup winning teams. Ozil’s transfer to Arsenal remains one of the most iconic deadline day signings

Mesut Ozil lifting FA Cup
Mesut Ozil lifting FA Cup

Gareth Bale – Tottenham to Real Madrid – 2013

Ozil left Madrid as mentioned above in the same transfer window, but it was okay because Los Blancos already had their newest Galactico lined up.

Gareth Bale left Tottenham Hotspur to join Real Madrid in a then-world record deal worth £85.3m. Despite injuries along the way, and then eventual problems with Zinedine Zidane, Bale’s career in the Spanish capital was special.

Over 100 goals for the club, five Champions League medals, three La Liga titles, one Copa del Rey and three Spanish Super Cups is not bad on a CV. Bale eventually left the club after nine years to join Los Angeles FC, but also had a loan spell at Spurs before that. This still remains one of the biggest deadline day signings in recent years.

Gareth Bale UCL 4
Gareth Bale UCL 4

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Pierre-Emerick Aubameyang – Borussia Dortmund to Arsenal – 2018

On deadline day of the January transfer window in 2018, Arsenal signed Pierre-Emerick Aubameyang for £56m, which at the time a club-record deal.

His time at Arsenal was full of ups and downs, but it got off to a steady start. The Gambian scored ten goals and recorded four assists in his debut season, and was the last player to score a goal under former manager Arsene Wenger.

The following season, he won the Premier League golden boot after netting 22 goals across the season. However, the award was actually shared with both Mohamed Salah and Sadio Mane, who both scored the same amount of times.

He eventually left North London in 2022, and had spells at Barcelona and Chelsea and now finds himself in Ligue 1 with Marseille.

 

Aubameyand Arsenal FA Cup
Aubameyang Arsenal FA Cup

Cristiano Ronaldo – Juventus to Manchester United – 2021

Cristiano Ronaldo returned to Old Trafford at the end of the summer transfer window in 2021, when Manchester United payed Juventus just shy of £13m for his signature.

The Portugal international produced an almighty second debut as many expected, when he scored a brace against Newcastle United. It was the start of good things to come, and he eventually scored 24 goals in all competitions on his comeback to the Theatre of Dreams.

However, things ended very sourly after he appeared in a controversial Piers Morgan interview, which aired live on TalkTV last November. He did not hide the fact that he wanted to leave, and ambushed the club, setting social media alight. Ronaldo left the club shortly after to join Saudi Pro League side Al-Nassr, where he is still playing now. This transfer still remains one of the biggest deadline day signings.

Ronaldo Piers Morgan
Ronaldo and Piers Morgan, before the end of his Manchester United career

Enzo Fernandez – Benfica to Chelsea – 2023

One of the most recent big deadline day signings was Enzo Fernandez’s move to Chelsea before the transfer window closed in January, earlier this year.

The Blues met Benfica’s £106m release clause just a couple of hours before the deadline. It is a British transfer record, and it was completed with very little time to go.

Fernandez won the World Cup with Argentina just a month or so before moving to West London, and he has become one of the first names on the Chelsea team-sheet. He is yet to live up to his £100m+ transfer fee, but he has still impressed in a blue shirt so far.

Enzo Fernandez
Enzo Fernandez

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