Transfer deadline day is now one of the most notable days in the football calendar – well, two if you count the winter one. It didn't actually exist in its current guise before 2002 but since then, things have gotten crazier and crazier.
Indeed, some of the Premier League's most notable transfers ever took place on the very last day of the window. Why do teams keep waiting until the last minute to do major business? No one is entirely sure – but it's made for some incredible headlines down the years.
So with that in mind, Football FanCast has gathered these picks for the most notable transfer deadline day deals in Premier League history.
10 Enzo Fernández joins Chelsea – 2023
We're going to the most recent deadline day for our first pick. Chelsea broke the British transfer record to sign Enzo Fernández from Benfica – something that seemed unthinkable a year ago.
For one, Enzo had only signed for Benfica six months prior and cost them a grand total of £10m. He started the season well and interest grew in him around a potential summer '23 move. Then the World Cup happened.
Enzo wasn't initially in Argentina's starting XI but forced his way in as the tournament went on. Eventually, he was a key part of their midfield as they won the trophy. The youngster was named the best young player at the tournament and transfer interest skyrocketed.
But no one actually thought a team would pay the £100+ asking price to sign him in January; surely only a summer move made sense? Enter Chelsea, who paid well over £100m (the Athletic) to sign Enzo. Benfica made a 10x profit in six months – quite the investment.
9 Liverpool sign Luis Suárez – 2011
There's not a lot of craziness around the actual deal here – Liverpool paid £22m (BBC) to sign Luis Suárez from Ajax in what was a fair price. He'd scored 49 goals in 48 games the previous season but a few Eredivisie players had done similar and then struggled after a transfer.
Suárez was also quite a controversial player after his brilliant 'save' in a World Cup quarter-final against Ghana (Luis Suárez is not a goalkeeper), while he had also been banned for biting an opponent earlier in the season. Still, Liverpool needed a new forward, and in came the Uruguayan.
What followed was one of the most notable careers in Premier League history. Suárez scored on his debut but was banned for alleged racial abuse before the end of the year. His second full season saw new manager Brendan Rodgers make him their main-man, though, and his goalscoring exploded, jumping from 11 in a season to 23.
Only, he was then suspended once again for biting an opponent just before the campaign ended. He returned to put in arguably the best individual season in PL history, equalling the record haul in 38-game season (31) while also adding double-digit assists. It was enough for Barcelona to sign him in the summer of 2014 – while, we should add, he was under a third suspension for biting.
8 Liverpool break record to sign Andy Carroll – 2011
Liverpool lost Fernando Torres at the deadline in January 2011 but moved to sign one of the most exciting young players in English football – Andy Carroll. Carroll had started the season in fantastic form for Newcastle United, looking like a one-man attack who just battered defences into submission.
He was energetic, massive, could score, could win headers, held up the ball well – just everything you wanted in a target man. Who better to replace Torres and partner new-signing Luis Suárez? £35m was a massive fee for someone with six months of PL football under their belt, but Liverpool felt Carroll was worth breaking their transfer record for.
He wasn't. Carroll looked out of place quite quickly and struggled badly in his first full season. Perhaps the fact Suárez was looking like magic next to him made things look worse than they were, but the Englishman just never got going. In fact, he'd never really recover the form he showed at Newcastle for the rest of his career.
Brendan Rodgers replaced Kenny Dalglish in 2012 and quickly decided he didn't need Carroll. Liverpool's record signing – and the most expensive English player ever – was out on loan 18 months after his arrival and never played for the Reds again.
7 Man United beat Man City to sign Dimitar Berbatov – 2008
Manchester United went into the summer of 2008 wanting a new striker. Dimitar Berbatov of Tottenham Hotspur was the man they really wanted – but it took a lot of work to get there.
And things nearly collapsed in the most ridiculous fashion right at the deadline. That summer was particularly notable because it ended with Manchester City being bought out by Abu Dhabi United Group. Suddenly, they were unfathomably wealthy but had about a day to throw the money around.
One of the things they did, though, was to bid for Berbatov right under the noses of United. They bid over £30m – a huge fee at the time – in attempt to steal the Bulgarian. Spurs accepted the offer, but Berbatov wasn't going to head to little old Man City.
He claims he 'never thought' about moving there and instead held out for United. They'd match City's bid and signed Berbatov in the final hour of the transfer window. Again, all of this happened in one day.
The signing was a massive statement for United, then, and a real power move over City and their money.
6 Chelsea spend big on Fernando Torres – 2011
Yes, here's a third one from the 2011 January transfer window – it's basically the 'Agueroooo' of transfer deadline days. We'll never see the likes of it again.
Fernando Torres's peak at Liverpool saw him as pretty indisputably one of the best strikers in the world. He could do absolutely everything and scored goals for fun – he was third for the Ballon d'Or in 2008, behind Cristiano Ronaldo and Kaka, having scored the winning goal as Spain won Euro 2008.
But one thing held him back – injuries. Torres struggled in 09/10 and didn't look quite right post-2010 World Cup. Still, he showed flashes of incredible quality, most notably scoring twice away at Chelsea as Liverpool won 2-0. Again, though, he seemed to have lost his pace and just moved a little slower than in previous years.
That's probably why Chelsea boss Carlo Ancelotti was reportedly not keen on the signing. Still, Roman Abramovich paid a British record £50m to sign him from Liverpool anyway – but it went as badly as it could.
Torres made his debut at home against Liverpool and lost 1-0. He followed that by struggling badly in front of goal – seriously, some of his misses were ridiculous, let alone for a player who was the best in the world two years prior. Torres didn't score for over 900 minutes and was just never the same player as he had been.
5 Man City make a statement with Robinho – 2008
Abu Dhabi United Group bought Manchester City at the transfer deadline in 2008 and wanted to make a statement. They eventually found one in Robinho, and it was one of the strangest signings ever made.
Even how they negotiated was strange. Real Madrid president Ramos Calderon explained years later that he essentially just kept asking for ridiculous things and was met with 'okay' at every turn. There was also the fact that Chelsea really thought they'd sign Robinho to the point where they sold shirts with his name on them before actually striking a deal.
But it was City who jumped in at the last moment to sign the Brazilian. The craziness was perhaps summed up by Robinho initially saying how wonderful it was to accept an offer from Chelsea, only for a journalist to ask if he meant Manchester City.
And to cap it all off, it turned out Robinho wasn't actually worth all the fuss. He was decent enough in his first campaign but City got rid of him within 18 months.
4 Real Madrid smash world record for Gareth Bale – 2013
Gareth Bale was a sensation in his last few years with Tottenham Hotspur. He could seemingly make anything happen with the ball, scoring ridiculous goals on an almost weekly basis.
And so there was a sense that we were all watching the next great player. Here was the possible next-Cristiano Ronaldo and a player who was about to start dominating. Real Madrid certainly saw it that way.
They had to wait a while but eventually struck a deal with Spurs on deadline day 2013. They paid what turned out to be a world record fee to get him, too (despite initially denying he'd cost more than Ronaldo). £85.1m was the final fee (Telegraph) and with that, Real had another Galactico.
Exactly how you judge Bale post-transfer is up for debate. He had some unbelievable moments, notably the 2018 Champions League final, while winning three La Liga title and five Champions Leagues. At the same time, he never found the consistency to be in that top, top bracket of player. Still, not a deal Real regret – Spurs will, though.
3 Tevez and Mascherano to…. West Ham? – 2006
Carlos Tevez and Javier Mascherano were two of the biggest talents in South America back in 2006. Maybe the two biggest. They were linked with massive clubs all over the world after shining for Corinthians in Brazil.
Only, Corinthians didn't actually own the players. A third party, Media Sports Investments, had the rights to both and looked to move them on that summer. It was a shock, to say the least, that West Ham United ended up with both. Two of the biggest talents in the game went to a mid-table Premier League side with little talk about it beforehand. How?
Well, this one got murky. It turned out that West Ham owned the registration rights to Tevez and Mascherano but not the economic rights. MSI still owned those. The Hammers were actually cheating here and would be fined by the Premier League for a breach of the rules. There were calls for them to be relegated, even.
To make matters worse, they also didn't think Mascherano was all that good – West Ham actually stopped playing him. He'd move to Liverpool the following January and go on to be an all-time great defensive midfielder. Tevez would move, too, but only after keeping the club up and becoming something of a legend there.
FIFA would outlaw third-party ownership in 2015, so we'll almost never see a story like this one again.
2 Ashley Cole ditches Arsenal for Chelsea – 2006
Ashley Cole was a huge success story of Arsenal's academy. He was England's left-back, a part of the Gunners' Invincibles side and well on his way to becoming the best in the world.
But then Chelsea showed interest. This was at the height of their power under Roman Abramovich, with him having bought the club in 2003. The Blues were throwing money around to sign the best they could.
Cole illegally met with Chelsea in 2005, without Arsenal's permission. This wasn't just a small meeting, either – Chelsea CEO Peter Kenyon was there, as was Blues boss José Mourinho. All were fined large amount once the Premier League got wind of it and no transfer was really possible that summer as a result.
But Cole still pushed. He made disparaging remarks about Arsenal in an autobiography written in early 2006 – he claims he nearly swerved his car off the road when hearing they'd 'only' offered him £55k per week.
By that summer, Chelsea and Arsenal engaged in talks and would eventually agree a deal of around £5m plus defender William Gallas. It went to the wire on deadline day, too, and wasn't announced until hours after time elapsed.
Gunners' fans were still outraged, though, labeling him 'Cashley' and condemning him to be a villain for life. It was one of the longest and fiercest transfer battles in Premier League history – and probably still tops that list to this day.
1 Wayne Rooney to Manchester United – 2004
Manchester United paid nearly £30m (Guardian) to sign Wayne Rooney back in 2004. If it hadn't worked out, he'd still be on this list for that was a crazy amount of money for a teenager back then – it was the record, in fact, breaking the £12m they'd paid for Cristiano Ronaldo the year before.
For context, Liverpool – who would win the Champions League that year – broke their outright transfer record that summer to sign Djibril Cissé for £14m. The Rooney deal was a risk, in other words.
But it was one worth taking. Yes, Rooney only had nine Premier League goals the previous season, but he was pretty unanimously seen as England's best player at Euro 2004 that summer. He was a very, very special talent and one that Sir Alex Ferguson wanted to take a chance on.
Everton, though, didn't really want to sell. It took a transfer request on August 27th to set things in motion and even then, the first offer that came in was from Newcastle United. The Toffees actually wanted to sell him to Chelsea, such was the money they were throwing around.
United were the ones to put up the cash, however, and it's safe to say there's no regret there. Not only was this a notable transfer for the time, but Rooney would go on to be both England and United's all-time top scorer while winning every trophy at club level. That massive risk turned out to be a bargain, and we may never see a deadline-day transfer as big as this one ever again.
