2003
Biggest deal:
Jonathan Woodgate (Leeds to Newcastle) – Flogged by Leeds for £9million in what many feared was their closing-down sale.
Best deal:
England centre-half Woodgate, when fit, proved himself to be worth the outlay by impressing during a season and a half under Sir Bobby Robson at St James’ Park. So much so that Real Madrid bought him while injured in August 2004 for £13.4million. It was to be over a year before he could make his debut, upon which he scored an own goal before being sent off.
Worst deal:
England’s Michael Ricketts moved to Middlesbrough from Bolton for £3.5million but scored just four goals in 38 matches. It was a busy deadline day for Boro, who also signed Malcolm Christie and Chris Riggott from Derby, as well as Brazilian midfielder Doriva. Juninho he was not.
Who the f***?
To soften the blow of losing Ricketts, Sam Allardyce went on a deadline day spree, with Bolton signing Salva Ballesta (a fascist, apparently…), Pierre-Yves Andre, Florent Laville and Ndiwa Lord-Kangana. The quartet managed 30 appearances between them.
2004
Biggest deal:
Jermain Defoe (West Ham to Tottenham) – The 21-year-old centre-forward moved across London for £7million plus Bobby Zamora.
Best deal:
The winter deadline day in 2004 was not a classic, in terms of either quality or quantity of deals. The Defoe/Zamora deals worked for both Spurs and West Ham with Defoe bagging 91 Premier League goals across two spells, while Zamora netted the winner in the following season’s play-off final to take the Hammers back to the top flight.
Worst deal:
None of the deadline day movers disgraced themselves, though Blackburn may have hoped for more from Jon Stead when they signed the 21-year-old centre-froward from Huddersfield for £1.25million. Still, eight goals in 42 Premier League games was enough for Rovers to a) stay up and b) make a profit when they sold him on to Sunderland a season and a half later for £1.8million.
Who the f***?
Jerome Thomas left Arsenal for Charlton for £100,000 having failed to make a first-team appearance in anything other than the League Cup, despite climbing through the England youth ranks. Yeah, January deadline day in 2004 was a stinker.
2005
Biggest deal:
Nicolas Anelka (Man City to Fenerbahce) – The France striker made the sixth move of his career, with a £7million deal taking his total fees to around £60million.
Best deal:
Michael Dawson made a £4million switch to Tottenham, who he would serve commendably for over a decade. But Everton pulled off the best deal (and one of the best January transfers of all time), taking Mikel Arteta on loan from Real Sociedad before sealing a permanent move for £2million in the summer.
Worst deal:
Eric Djemba-Djemba was bad for Man Utd but he was even worse for Aston Villa after moving to Villa Park for £1.5million. For that sum, Villa got 11 Premier League appearances in two and a half years.
Who the f***?
Portsmouth signed striker Aleksandar Rodic from Slovenian champions Gorica but the 24-year-old started just one game for Pompey being shipped out to Turkish club Kayserispor.
2006
Biggest deal:
Robert Earnshaw (West Brom to Norwich) – The Wales striker moved to Carrow Road for £3.5million, with the Championship club forking out the highest fee on deadline day.
Best deal:
David Bentley joined Blackburn on a permanent deal after spending the first half of the season on loan from Arsenal. It was an undisclosed fee, but Arsenal were said to have raked in £7million due to a 50 per cent sell-on clause when the midfielder subsequently moved to Spurs.
Worst deal:
Hossam Ghaly joined Tottenham for an undisclosed fee but however much they paid Feyenoord, it was too much.
Who the f***?
Andrés D’Alessandro made a huge impression at Pompey during a 13-game loan spell from Wolfsburg. He’s best remembered, though, for having had a tattoo of his own face on his midriff.
Lionel Scaloni joined West Ham on loan from Deportivo La Coruna and is yet to be forgiven in east London for sportingly putting the ball out of play in the last minute of the FA Cup final, which ultimately led to Steven Gerrard’s last-gasp equaliser.
2007
Biggest deal:
Matthew Upson (Birmingham to West Ham) – The centre-half made the move to Upton Park for £6million. Upson proved to be an smart purchase, even if he was skipper during their wretched 2010-11 campaign which ended in relegation under Avram Grant.
Best deal:
Liverpool had a belting deadline day. Alvaro Arbeloa arrived for £2.6million from Deportivo La Coruna while Javier Mascherano was signed initially on loan from West Ham.
Worst deal:
Watford, desperately trying to stave off relegation, spent £600,000 on Gareth Williams from Leicester. The Scotland midfielder managed only three appearances before injury cut short his career.
Who the f***?
Johan Cavalli, a Corsican midfielder also joined Watford from French side Istres on a free transfer. Three appearances in six months and and a relegation later, he had his contract terminated.
2008
Biggest deal:
Afonso Alves (Heerenveen to Midlesbrough) – Boro smashed their transfer record by spending £12.7million on the Brazil striker who scored 45 goals in 39 Eredivisie matches…
Best deal:
Portsmouth also signed a goalscorer, with Jermain Defoe moving again on deadline day in a £7.5million deal from Tottenham. Fifteen goals in 31 Premier League appearances later, Pompey sold Defoe back to Spurs for twice what they paid.
Worst deal:
Alves turned out to be one of the biggest flops in Premier League history. He managed only 10 goals in 42 Premier League appearances over a season and a half for Boro, who were relegated before Alves was flogged to Qatar for £7million.
Who the f***?
Nouveau-riche Man City signed Felipe Caicedo from Basel for £5.2million. The Ecuador striker was described as “one of the great South American talents”, though no one knows who said that. A haul of four goals suggests it might have been his mum.
2009
Biggest deal:
Andrey Arshavin (Zenit St Petersburg to Arsenal) – The winter’s most tortuous deal was also its priciest, with the Russia playmaker eventually confirmed as a £15million Arsenal player 24 hours after the window closed.
Best deal:
Six months after sending Robbie Keane to Liverpool for £20million, Tottenham bought the striker back for £12million. Keane hardly set the world alight during his second spell at White Hart Lane but it was the easiest money Daniel Levy has ever made.
Worst deal:
Ricardo Quaresma said his Chelsea loan from Inter Milan “brought back the joy”. One start and four substitute appearances which produced one assist suggests he is easily pleased.
Who the f***?
West Brom signed Argentine winger Juan Carlos Menseguez from San Lorenzo on loan until the end of the season. After scoring on his debut, he did little else of note before disappearing back to Argentina.
2010
Biggest deal:
Adam Johnson (Middlesbrough to Man City). The England winger joined Roberto Mancini’s City for £7million.
Best deal:
Asmir Begovic’s £3.25million move from Portsmouth to Stoke was a masterstroke. The Bosnia keeper established himself as one of the Premier League’s best before opting to sit on the Chelsea bench in 2015.
Worst deal:
West Ham signed three strikers – Mido from Middlesbrough, Brazilian Ilan from St Etienne and Blackburn forward Benni McCarthy – taking the total number of forwards in Gianfranco Zola’s squad to nine. The three signings reaped a total four goals, all of which were scored by Ilan.
Who the f***?
Marcelo Martins Moreno joined Wigan on loan from Shakhtar Donetsk. A Bolivian forward, apparently. Not that any of us remember him…
2011
Biggest deal:
Fernando Torres (Liverpool to Chelsea) – The Spain striker moved to Stamford Bridge for £50million on a frankly mental deadline day.
Best deal:
Liverpool immediately reinvested the money they received for Torres by buying two strikers. The £23million signing of Luis Suarez from Ajax went rather well…
Worst deal:
Their £35million purchase of Andy Carroll from Newcastle did not. The striker scored just 11 goals in 58 appearances before Brendan Rodgers shipped him off to West Ham, with the Reds taking a £20million hit.
Who the f***?
Blackburn boss Steve Kean was very excited by the permanent signings of Ruben Rochina and Mauro Formica. Striker Formica scored five goals in 55 appearances, while Rochina fared slightly better with seven in 46.
2012
Biggest deal:
Kevin De Bruyne (Genk to Chelsea) – The Belgium international was loaned back to Genk immediately after signing a permanent deal at Stamford Bridge for £6.7million.
Best deal:
An uneventful deadline day, upon which Nikica Jelavic to Everton and Spurs signing Louis Saha were the only other moves of note, mean that Chelsea’s purchase of De Bruyne was the best deal, purely because they made a profit of around £11million when they sold him to Wolfsburg 18 months later.
Worst deal:
Man Utd eventually gave up on Ravel Morrison and sold the troubled teenage prodigy to West Ham for an undisclosed fee. “A brilliant footballer. Brilliant ability. Top class ability. Needs to get away from Manchester and start a new life,” said Sam Allardyce, but a change of scene failed to have the desired effect.
Who the f***?
Arsenal signed Thomas Eisfeld from Borussia Dortmund for £440,000 but the attacking midfielder failed to make a Premier League appearance for the Gunners.
2013
Biggest deal:
Mario Balotelli (Man City to AC Milan) – Balotelli had long since been written off by Roberto Mancini and his £19million exit was at least half a season overdue.
Best deal:
Stoke have signed their last two No.1s on the final day of the January window, with Jack Butland making a £3.5million move from Birmingham. Five years later, he has been linked with a £40million move to Liverpool. Everton signing John Stones from Barnsley for £3million went quite well too…
Worst deal:
QPR signed Christopher Samba for £12.5million on a four-and-a-half-year contract with Harry Redknapp hoping the £100,000-a-week centre-half could shore up his woeful defence. Within three months, he was telling Rangers fans to “grow up and get over his wages”. Luckily for QPR, upon their relegation, Anzhi Makhachkala were willing to give them their money back. Danny Graham had a nightmare at Sunderland after his £5million switch from Swansea.
Who the f***?
Kevin Mbabu joined Newcastle from Servette, much to the delight of ‘Shooting Stars’ fans. Sadly, the versatile defender was deprived of the chance to establish himself at St James’ Park and returned to Switzerland after five appearances in three-and-a-half years.
2014
Biggest deal:
Kurt Zouma (St Etienne to Chelsea) – The young centre-half completed a permanent move to Stamford Bridge for £12million before being loaned back to the Ligue 1 side.
Best deal:
It wasn’t a classic deadline day. Crystal Palace, under new boss Tony Pulis, were struggling to stay out of the drop zone, and were rock bottom in mid-January. The deadline day signings of Scott Dann, Wayne Hennessey, Joe Ledley and Jason Puncheon helped the Eagles climb the table and get on a solid footing in the Premier League.
Worst deal:
Fulham spent £11million on Greece striker Konstantinos Mitroglou in the hope of staving off relegation. Mitroglou made three appearances for the Cottagers, failing to find the target, before they were relegated.
Who the f***?
Arsene Wenger’s purchase of Kim Kallstrom from Spartak Moscow provoked bemusement everywhere, not because he was an unknown, but because no-one knew why the hell Arsenal were signing him.
2015
Biggest deal:
Juan Cuadrado (Fiorentina to Chelsea) – Mo Salah moved the other way on loan while Chelsea took the Colombian winger for £23.3million.
Best deal:
Tottenham signed Dele Alli for £5million before loaning him back to MK Dons. Turned out quite well, that. Man Utd were feeling generous, giving West Brom Darren Fletcher for free and sending Wilf Zaha ‘home’ for £15million.
Worst deal:
Chelsea cannot claim that the Cuadrado deal worked out as they would have wished. His arrival squeezed out Salah, while Cuadrado spent the vast majority of his Chelsea career on loan at Juve before the Blues took a £6million hit on the winger when he joined Juve permanently last year.
Who the f***?
Having been linked with Mats Hummels, Kevin Strootman and Marquinhos during the window, Manchester United’s only deadline day arrival was Bolton full-back Andy Kellett. The 21-year-old was signed on loan to provide cover for the reserves, much to United fans’ bemusement.
2016
Biggest deal:
Giannelli Imbula (Porto to Stoke) – The Potters smashed their transfer record by paying £18.3m for the French midfielder. Eighteen months later, he was loaned out to Toulouse.
Best deal:
There was not a single stand-out hit from February 1, 2016. Watford’s £16million purchase of Abdoulaye Doucoure has proved to be a savvy bit of business, though.
Worst deal:
Oumar Niasse’s resurgence at Everton means Imbula must be regarded as the worst deal of a deadline day during which none of the top eight entered the market.
Who the f***?
Newcastle spent £29million during January in the hope of escaping relegation but while Andros Townsend and Jonjo Shelvey were sound purchases, Seydou Doumbia and Henri Saviet most certainly were not. The Championship beckoned.
2017
Biggest deal:
Manolo Gabbiadini (Napoli to Southampton) – The Italy striker joined Saints for £14.6million having attracted the attention of pretty much every mid-table side.
Best deal:
Palace spent a similar undisclosed amount on midfielder Luka Milivojevic from Olympiakos as well as signing Mamadou Sakho on loan from Liverpool. The pair helped the Eagles climb out of the drop zone and finish 14th.
Worst deal:
Hull made three signings on deadline day: Alfred N’Diaye and Andrea Ranocchia, while Kamil Grosicki arrived on a permanent deal. None were especially terrible, though neither did they enhance the Tigers’ survival hopes.
Who the f***?
As well as Gabbiadini, Southampton also signed Mouez Hassen on loan from Nice. The former France Under-21 international didn’t play a game for Saints.
2018
Biggest deal:
Pierre-Emerick Aubameyang (Dortmund to Arsenal) – We were still looking for the catch by the time Arsenal announced the club-record signing of an elite striker at peak age, having faced absolutely no competition whatsoever. Aubameyang became the quite literal fastest Arsenal player to 25 Premier League goals on Tuesday.
Best deal:
Aubameyang’s closest rival here would be either Lucas Moura or Olivier Giroud, which says it all.
Worst deal:
Watford loaning Sunderland flop Didier Ndong was weird, and Swansea spending a club-record fee on Andre Ayew before relegation was silly, but Stoke bought Badou Ndiaye for £13.9m, saw him have little to no impact, and loaned him out five months after he joined.
Who the f***?
Twenty-three goals in 103 Championship games at the age of 25 was enough to persuade West Ham to part with £10m for Jordan Hugill. The former Preston striker played just 22 Premier League minutes, and promptly joined Middlesbrough on loan in August. The good news is that he hasn’t missed a step: he has six goals in 22 league games for them.
Ian Watson