Twenty years of Deadline Day: The best Premier League signings from 2002-2022

Twenty years of Deadline Day: The best Premier League signings from 2002-2022
Twenty years of Deadline Day: The best Premier League signings from 2002-2022
Twenty years of Deadline Day: The best Premier League signings from 2002-2022
It may feel like there was never a time before the transfer window and the climax of it all - Deadline Day. But in the Premier League it’s still a relatively modern conception. Before the 2002-2003 season, players were able to move freely through the season until March 31st when there was a deadline of sorts. But 20 years ago, it was the first time teams had to get their squads sorted in the summer. 

Here, we chart the best signing from every summer transfer window. This may not be the player who changed the face of the Premier League but a player that raised eyebrows and got people talking. 

2002: Robbie Keane (Leeds United to Tottenham Hotspur, £7m)

Ok, so the first transfer deadline day was a bit of a dud. Only four moves were made on that day, but there were two notable ones. Firstly, Ivan Campo moved on loan from Real Madrid to Barcelona before Robbie Keane switched Yorkshire for London. 

Seven million may not sound a lot today, but 20 years ago, this was a big sum to pay. Keane would go on to spend six years in London before moving to Liverpool. His best season in front of goal came in the 2006-07 season when he netted 15 times in the league. 

2003: Claude Makelele (Real Madrid to Chelsea, £16.6m)

This was the summer of Chelsea and the summer of Abramovich. The Russian oligarch had bought the club back in June and was not afraid to put his money where his mouth was. Spending big on Hernan Crespo, Damien Duff and Juan Sebastian Veron was a big statement, but there was none who were as influential as Claude Makelele. 

With Chelsea, he became a midfield commander, even having a role named after him on the field. He would be there for five seasons, winning the Premier League and FA Cup, League Cup. 

Jose Mourinho declared him Chelsea’s Player of the Year in their title-winning season of 2004-05 - money well spent.

2004: Wayne Rooney (Everton to Manchester United, £20m)

A once-in-a-generation talent, Wayne Rooney signed for Manchester United on deadline day in 2004. The mercurial forward had made people aware of him on his debut as a 16-year-old, when he scored a miraculous volley against Arsenal for Everton. From that moment, it seemed he was destined for greatness. 

Not much more needs to be said about his time at United. He won everything at club level and became their all-time leading goalscorer. A legend on the pitch.

2005: Michael Owen (Real Madrid to Newcastle United, £17m) 

We had to pick this as a helicopter was involved. The transfer of Michael Owen to Newcastle United feels like a sea-change in transfers and transfer sagas. A broken transfer record by the north-east club was needed to bring Owen to St James’ Park and the fanfare was off-the-charts. 

More than 20,000 fans turned up to see their new forward, who landed on the pitch in the chopper, but this positivity did not last long. Over the four years of injury-hit football with Newcastle, he only netted 26 league goals and would eventually leave for Manchester United. 

2006: Ashley Cole (Arsenal to Chelsea, £5m)

Exactly 140 transfers were made on this particular deadline day in English football, but none more full of drama than Ashley Cole’s move across London to Chelsea. 

At the time, he was one of the best left backs in the world and this saga had been 18 months in the making. Back in January 2005, Cole’s representatives met with Chelsea’s executives to make a move happen, something Cole insists that the talks were never about a transfer. Even so, Chelsea were fined for the talk.

Over the next year and a half, tensions between Arsenal and Cole reached boiling point - he was left out of squad photos and was understood to not be offered an improved contract. In the end on deadline day, he was sold to Chelsea and with William Gallas going the other way, this saga came to an end.

2007: Glen Johnson (Chelsea to Portsmouth, Undisclosed fee)

An interesting fact about the 2007 Deadline Day was that the most money spent where the fee was disclosed was just one million pounds. 

Glen Johnson’s move from Chelsea to Portsmouth is one of those undisclosed fees - reported to be near £4million. Frustrated at Chelsea with lack of game time, Johnson’s move to the south coast was when Pompey were riding high and Johnson had already spent a season on loan with the club in 2006. 

He would go on to lift the FA Cup with Portsmouth, play in Europe and get his big money move to Liverpool. Portsmouth, on the other hand, have never reached those heights again, now plying their trade in England’s third tier.

2008: Dimitar Berbatov (Tottenham Hotspur to Manchester United, £30.8m)

Now, this was chaos. Manchester City had been taken over by current owner Sheikh Mansour ON Deadline Day and the new owners were ready to make a splash. 

Chelsea were looking to buy Robinho from Real Madrid. Whilst they were doing that United had their eyes on Berbatov, but Spurs would only allow City to speak to Berbatov. But, the Bulgarian wanted to move to the red side of Manchester. City decided to cut their losses and go after Robinho themselves. Keeping up?

With this three-way tug-of-war over two players, Manchester United got their man and Berbatov moved to Manchester to create one of the most threatening strike forces assembled in Premier League history alongside Wayne Rooney and Carlos Tevez. 

Robinho struggled to make an impact with City, leaving 18 months later. 

2009: Niko Kranjcar (Portsmouth to Tottenham Hotspur, Undisclosed fee)

Back to Tottenham and it would be remiss of us not to mention the deals of Harry Redknapp when talking about deadline day deals. He had his fingerprints on plenty of last-minute purchases and Nico Kranjcar was one of those who Redknapp trusted wherever he went.

It was his second deadline move after moving to Portsmouth and to Redknapp, and Kranjcar enjoyed a relatively successful spell with Spurs before being phased out due to the rise of one Gareth Bale. He left in 2012, heading for Dynamo Kyiv. Redknapp wasn’t the manager, however.

2010: Asamoah Gyan (Rennes to Sunderland, £10m)

This transfer was one of those that felt like it came out of nowhere. Gyan had been relatively prolific in Ligue 1, but he came to the attention of Premier League fans with his cool finishing and his cool dance moves. Incredibly it felt like he was in the northeast for a few years, but he was there for only one full season, moving on the next summer. 

It wasn’t for a long time, but it was certainly a good time.

2011: Mikel Arteta (Everton to Arsenal £10m)

What do you do after you lose 8-2 to one of your rivals? Well, if you’re Arsene Wenger, you have a crazy deadline day and sign five players. Some could be considered a mistake - Andre Santos - but some did work. Per Mertesacker became vice-captain, which he proudly displays on his LinkedIn page, and Mikel Arteta, who would later become the club manager. 

As a player, Arteta was dependable and solid. He had a great eye for a pass but could also defend resolutely. After losing Cesc Fabregas that summer, Arteta was a good replacement. He fared well for Arsenal and finished his career there before coming back as head coach three years later.

2012: Hugo Lloris (Lyon to Spurs, £8m)

Lloris joined Spurs from Lyon on the last day of the 2012/13 summer transfer window for a fee of £8 million. Considering the price tag, the London side and its supporters would all tell you that it was one of their history’s biggest investments.

The World Cup winner is seen as one of the greatest goalkeepers of his generation, he was eventually captained by Argentinian manager Mauricio Pochettino in 2015. Lloris also lead Tottenham out of the tunnel as they lost to Liverpool in the 2019 Champions League final.

2013: Mesut Ozil (Real Madrid to Arsenal, £42.5m)

Heading to the other side of London, this is one the Gunners will never forget. A deal that resonated highly in the Premier League and there is no other way of saying this, one for the history books.

The most expensive German player (at the time) had joined from none other than Real Madrid. An eight-year spell in London where he was shortlisted for the Ballon d’Or, ended a trophy drought with three FA Cups and a community shield and unforgettable moments of magic.

2014: Sadio Mane (RB Salzburg to Southampton, £10m)

Looking back at it now, £10 million for the Senegal international is, to say the least, a steal. Finishing his last campaign with Southampton as the side’s top scorer and an impressive form towards the end of the season earned a place in Jurgen Klopp’s Liverpool.

The rest is pretty much history. Mane became an integral part of the side that brought the Premier League trophy back to Merseyside for the first time in 30 years, as well as Champions League glory in 2019.

2015: Michail Antonio (Nottingham Forest to West Ham, £7m)

From non-league to Premier League, the climax of Michail Antonio’s climb up the English football ladder was when he joined West Ham from Nottingham Forest.

Antonio started off as a full-back to eventually becoming one of the Premier League’s most annoying strikers, just ask Pep Guardiola! A versatile player with a remarkable presence on the pitch (and off it as well) who has been a gem to the Hammers’ dugout through the years.

2016: David Luiz (PSG to Chelsea, £34m)

The return of David Luiz to Stamford Bridge after a short spell at PSG was vital to Antonio Conte’s title-winning Chelsea team.

Part of the three-man defence that imposed the Italian’s ‘Catenaccio’ to dominate the Premier League in an unconventional way. It was no surprise when he made it to the PFA Premier League team of the year.

2017: Alex Oxlade-Chamberlain (Arsenal to Liverpool, £35m)

While he might have not fulfilled his potential due to injuries, Chamberlain’s move to Liverpool from rivals Arsenal after a six-year spell there was helpful to the Jurgen Klopp era.

He showed great promise to be part of the Champions League and Premier League winning side, however, has only managed 17 goals and 15 assists in 133 appearances for the Reds.

2018: Lucas Moura (PSG to Spurs, £23m) 

That hat-trick in Amsterdam in the Champions League semi-final was simply unforgettable, while Spurs failed to complete the feat and lift the trophy, his name will most likely forever be forged into the London side’s history.

A versatile and an important part of Tottenham, Lucas has made over 100 appearances in all competitions.

2019: Romelu Lukaku (Manchester United to Inter Milan, £73m)

The only player in this article to leave the Premier League, but his time at Inter prompted Chelsea to spend more than £90million to bring him back a season later. Whether at Manchester United or at Chelsea, Lukaku struggled to live up to the price tag set for him. 

That is of course not his problem, he can’t help the money aspect of the game, but his time with Inter should be considered his best. Scoring goals for fun in Serie A, he gave that infamous interview whilst at Chelsea speaking of his love for the fans in Milan. 

At United, he scored at around a goal every other game across two seasons - not enough to be considered top class at such an illustrious club. 

2020: Raphinha (Rennes to Leeds United, £17m)

Raphinha joined Leeds from Rennes after scoring eight goals and assisting seven with the Ligue 1 side, joining the English club as they were celebrating their return to the Premier League after a decade of absence.

His flair and performances in big games helped them stay in the top tier of English football in dramatic fashion. His display at Brentford last season helped Leeds stay up in the Premier League, he was eventually sold for a minimum of 50 million to Barcelona, a sum that will likely be helpful to Leeds.

2021: Cristiano Ronaldo (Juventus to Manchester United, £19.8m)

In retrospect, this transfer did not produce as much as everyone expected, especially considering the saga that took place in this past window. 

However, the effect it has had on the football world cannot go unnoticed, suffice to say that it produced the football-related social media post with the most engagement in history as well as shirt sales that were reported to have broken the all-time record following a transfer.

Ronaldo became the team’s top scorer with 18 goals in the league as well as six in the Champions League, a few of those came at vital times and helped United go as far as the round of 16.