Ranked! The Premier League's 10 best deadline day deals EVER

Arsenal manager Arsene Wenger with new signing Mesut Oezil at London Colney on September 12, 2013 in St Albans, England.
(Image credit: Getty Images)

We all love a good deadline day saga. Clubs spending ludicrous sums of cash on players they've never heard of, fax machines mysteriously breaking down and windows rolling up and down in an endless loop of car-based interviews. 

This year there has been a little less chaos (so far) this window but it's impossible to forget the madness of yesteryear. Madness that should be celebrated as one of the many reasons we all love this crazy game.

Trolley dashing doesn't have to be bad, as these brilliant deadline day signings prove…

10. Marouane Fellaini – Standard Liege to Everton, 2008 (£15m)

Marouane Fellaini

Fellaini made an instant impact in England after joining Everton in September 2008 - not because of his unique hairstyle or flailing elbows, but thanks to his ability to cause chaos inside opposition boxes bombing forward from midfield. 

He was named the club’s young player of the year in his debut campaign and gradually established himself at Premier League level under David Moyes’s tutelage. In five years in the blue half of Merseyside, he made 177 appearances and scored 33 times.

It wasn’t a surprise, then, when Moyes brought him to Old Trafford via another deadline-day signing in 2013. That time it cost him almost £28m, though – and the wrath of Manchester United fans. Not least as his £23m release clause had expired at the end of July. 

9. Dimitar Berbatov - Tottenham to Man Utd, £30.75m

Dimitar Berbatov poses with Sir Alex Ferguson and a Manchester United shirt after signing for the club at Old Trafford on September 1, 2008 in Manchester, England.

(Image credit: Getty Images)

This was one of the sagas of the 2008 summer window. It was a move United supporters were desperate to happen and they got their wish at the eleventh hour, almost literally. Sir Alex Ferguson finally got his man in a deal worth a little over £30m for the irresistible Bulgarian striker.

In four seasons at Old Trafford, Berbatov produced some incredible highlight-reel moments and became a two-time Premier League champion. In 149 appearances, he scored 56 goals and assisted 27 times for the Red Devils and will always be a fan favourite.

8. Robbie Keane – Leeds to Tottenham, 2002 (£7m)

It's fair to say that Leeds probably should have asked a bigger fee from Tottenham for Keane. At just £7m, the Irish striker was an absolute steal – not least as he'd cost Coventry £6m in 1999, Inter Milan £13m a season later, and then Leeds £12m in May 2001.  

Keane spent nine years at White Hart Lane over two spells between 2002 and 2011, broken up by a six-month stint with Liverpool (from which Spurs received £19m), plus loans at Celtic and West Ham. In 303 appearances he scored 122 goals – enough for him to rank among the top 10 goalscorers in Spurs history... until Harry Kane came along. 

That he was named Spurs’ player of the season three times – including in his debut campaign – outlines the Irishman's level of performance. A pity, though, that he only lifted a solitary League Cup title in his time there.

7. Carlos Tevez – Corinthians to West Ham, 2006 (Undisc.)

Carlos Tevez, Javier Mascherano

Jaws dropped when West Ham signed the Argentine duo, who arrived at Upton Park with pedigree and promise. 

Mascherano, then 22, struggled to establish himself (famously falling behind Hayden Mullins in the pecking order) and left on loan to Liverpool in January 2007 – although he netted West Ham a huge £18.5m when the move was made permanent at the end of that season.

Tevez, on the other hand, almost singlehandedly saved the Hammers from relegation. With 10 games to go and the east Londoners languishing in the bottom three, he scored seven times – including the all-important winner against Manchester United at Old Trafford on the final day of the season – to help West Ham claim seven victories and finish three points above the drop zone.

6. Ashley Cole – Arsenal to Chelsea, 2006 (£5m)

Ashley Cole

Cole can be considered one of the greatest bargains in Chelsea’s history, having moved to Stamford Bridge for just £5m. Granted, the Blues had to give up William Gallas as part of the deal, but what Cole helped the club achieve more than proved his worth.

In eight years at Stamford Bridge, the ex-England international won as many major honours, including one Premier League crown, four FA Cups and the 2012 Champions League – Chelsea’s first ever triumph in the competition. In total, he made 338 appearances and scored seven times.

5. Hugo Lloris – Lyon to Tottenham, 2012 (£8m)

Lloris was once touted as a potential rival to Manuel Neuer as the best goalkeeper in the world, so it was surprising when Tottenham managed to sign him for a relatively cheap £8m in 2012.

Since then, the French goalkeeper has become captain of both club and country, leading from the back with command and consistency – as he demonstrated during France's victorious World Cup campaign in 2018. At 34, he's now getting on a bit, but could still be a mainstay at Spurs for a few years yet. 

4. Mesut Ozil - Real Madrid to Arsenal, 2013 (£42.5m)

New Arsenal signing Mesut Oezil at London Colney on September 12, 2013 in St Albans, England.

(Image credit: Getty Images)

Arsene Wenger made one of the signings of 2013 when he landed Mesut Ozil for around £42.5m. The German playmaker’s arrival at the Emirates was one that sparked immense excitement and he repeatedly showed why he was box-office viewing, while throwing in the odd clanger for good measure.

An enigmatic talent and, perhaps, individual, Ozil was borderline unplayable on his day and should rightly be remembered as one of the Premier League’s greatest coups.

He made 254 appearances for the Gunners in all competitions, scoring 44 goals and notching 79 assists before being swiftly moved on when Mikel Arteta took the reins.

3. Claude Makelele – Real Madrid to Chelsea, 2003 (£16m)

Claude Makelele

Makelele was often referred to as the most important player within a Real Madrid team filled with Galacticos, to the point that even the usually-reserved Zinedine Zidane aired his disgruntlement when his compatriot was sold to Chelsea in 2003. 

In total, he made 217 appearances for the Blues and became an essential element of Jose Mourinho’s dominant team that claimed back-to-back league titles in 2005 and 2006 – so much that a position on the pitch was named in his honour. In his final season in London, he helped guide Chelsea (then under Avram Grant) into their first ever Champions League final... where they lost on penalties to Manchester United.

2. Luis Suarez – Ajax to Liverpool, 2010 (£22.8m)

Forget the controversies for a second: Suarez's signing was one of the greatest deals in Liverpool's history, at a time when they were making many bad ones. In four seasons on Merseyside, the Uruguayan scored 82 goals in 133 appearances and earned cult hero status, helping Liverpool fans move on swiftly from Fernando Torres.

While he couldn't quite guide the Reds to the title – they fell just short in Suarez’s last season of 2013/14 – he did help them win the League Cup in 2012 and earned a host of individual honours, including Liverpool Player of the Season twice and the PFA Player of the Year in 2014.

His eventual transfer to Barcelona also netted Liverpool a hefty profit in the region of £42m.

1. Wayne Rooney – Everton to Man United, 2004 (£20m)

Wayne Rooney

The images of Rooney as a teenage tyro are long faded, but for a decade he was essential to Manchester United's cause as they dominated the Premier League and triumphed on the continent. 

By the time of his return to first club Everton in 2017, Rooney had 253 goals at Old Trafford – making him the club's all time record goalscorer – and 11 major honours to his name.  

He was also named in the PFA Team of the Year three times, was the PFA Player’s Player of the Year in 2009/10, PFA Fans’ Player of the Year twice and the PFA Young Player of the Year twice. A bona fide Stretford legend. 

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Joe Brewin

Joe was the Deputy Editor at FourFourTwo until 2022, having risen through the FFT academy and been on the brand since 2013 in various capacities. 


By weekend and frustrating midweek night he is a Leicester City fan, and in 2020 co-wrote the autobiography of former Foxes winger Matt Piper – subsequently listed for both the Telegraph and William Hill Sports Book of the Year awards.