Michael Owen for Antonio Nunez + £8m
Liverpool and Real Madrid
After maintaining his one-in-two strike rate in his final season at Liverpool in 2003/04, Owen was sold to Real Madrid for a fee of £8m plus Nunez. That represented an excellent deal for los Blancos, who took full advantage of the fact that the England striker only had a year remaining on his contract at Anfield.
Owen didn’t set the world alight at the Santiago Bernabeu, although he did end the campaign with a better minutes-per-goal ratio than any of his team-mates. Nunez, an unused substitute in Liverpool’s Champions League victory over Milan, did little of note on Merseyside and was sold to Celta in 2005.
Jermain Defoe for Bobby Zamora + £7m
West Ham and Tottenham
A rare swap deal which worked out pretty well for all parties. Defoe had been part of the absurdly talented West Ham side that got relegated with the highest points total in Premier League history, and after scoring 11 in 19 second-tier games it was no surprise that he found a suitor in David Pleat's Spurs.
Zlatan Ibrahimovic for Samuel Eto’o + £35m (and Alexander Hleb on loan)
Inter and Barcelona
In search of a plan B for when Barcelona’s tiki taka wasn’t bearing fruit, Pep Guardiola signed Ibrahimovic from Inter in summer 2009. Eto’o, meanwhile, had a difficult relationship with the Blaugrana boss, so was included in a deal which also sent £35m and Hleb to San Siro.
Ibrahimovic scored 21 goals in 45 appearances for Barcelona, but he was unhappy at playing second fiddle to Lionel Messi and left the following summer. More literally, Eto’o was also placed in an unfamiliar position at Inter – Jose Mourinho deployed him out wide in many of the Nerazzurri’s biggest games – but the Cameroonian was at least rewarded with Serie A, Champions League and Coppa Italia winner’s medals.
David Luiz for Nemanja Matic + £20m
Benfica and Chelsea
Chelsea’s policy of hoarding every promising youth player under the sun does occasionally lead to some odd transfer dealings. One such move came in 2011, when the Blues’ desperation to sign Luiz from Benfica saw them include promising midfielder Matic in the deal.
It’s tough to pick a winner in this one – Benfica certainly did well financially, later selling Matic back to the Blues for £21m, but Chelsea ultimately got the best of both players on the pitch.
Roberto Carlos + £1m for Ivan Zamorano
Inter and Real Madrid
Chilean forward Zamorano was one of the most coveted strikers in Europe back in 1995, having notched 28 goals in 38 games to help Real Madrid to the La Liga title. The emergence of Raul cost him game time at the Bernabeu, though, so Roy Hodgson’s Inter stepped in and sent Roberto Carlos in the opposite direction.
The Brazilian, who later claimed Hodgson’s stint at San Siro “destroyed” him, would soon establish himself as one of the world’s best left-backs. Zamorano was far from a failure in Italy, scoring 40 in 148 games – but he’s probably best remembered for wanting the No.9 shirt (occupied by Ronaldo) so badly that he put a plus sign between the ‘1’ and ‘8’ on his back.
Ricardo Quaresma for Deco
Porto and Barcelona
Barcelona won the race for his signature, their bid presumably aided by a willingness to sweeten the deal by including Quaresma – who had been in a similar position to his international team-mate a year earlier. It did the trick, but whereas the latter struggled to fulfil his potential back in Portugal, Deco won two leagues, two cups and the Champions League at the Camp Nou.
Francesco Coco for Clarence Seedorf
Milan and Inter
One of the biggest mistakes Inter have ever made was allowing Andrea Pirlo to join city rivals AC Milan in 2001. Their decision to exchange Seedorf for Coco a year later was almost as bad; while the Dutchman went on to win two Champions Leagues and two Scudetti in red and black, the Italian played just 26 league games in five years on the Nerazzurri’s books.
Still, at least Inter learned their lesson and definitely didn’t sell a young Leonardo Bonucci – who’s now at Milan – to Genoa in 2009. Hang on, what’s that?
William Gallas for Ashley Cole + £5m
Chelsea and Arsenal
Gallas reportedly threatened to deliberately score own goals if he wasn’t allowed to leave Chelsea in 2006 (something he later refuted to FFT), so you can see why Arsenal were keen to snap him up. The centre-back proceeded to fall out with team-mates at the Emirates and, despite being captain, once sat down in the centre-circle in an epic sulk after a draw with Birmingham.
Cole, on the other hand, was a fixture at left-back for the Blues, winning the league, four FA Cups and the Champions League. He did also shoot an unsuspecting work experience kid with an air rifle, though, so it’s swings and roundabouts.
Andrew Cole for Keith Gillespie + £6m
Newcastle and Manchester United
In fact, Gillespie was the less surprising half of a swap deal with the Geordies' goal machine Andy Cole. The Londoner wasn't seeing eye-to-eye with Kevin Keegan, who was forced to explain his decision to irate fans outside St James' Park. Fergie acted as impromptu agent for Gillespie, wangling the Ulsterman a 380% pay-rise; he also considered buying him back that summer, instead opting to promote some kid called David Beckham. Cole won five league titles and the Champions League at Old Trafford.
Fabio Cannavaro for Fabian Carini
Inter and Juventus
In 2004, Inter shipped out Italy’s future World Cup-winning captain in a swap deal for Uruguayan goalkeeper Carini. Cannavaro went on to form part of the Old Lady’s incredible defence alongside Lilian Thuram and Gianluca Zambrotta, and in front of Gianluigi Buffon, before joining Real Madrid after the Calciopoli scandal in 2006.
Conversely, Carini struggled to break into the first team at Inter, making just four appearances for the club during a three-year spell, most of which was spent out on loan. There’s only one winner here.
Ian Wright for some weights
Crystal Palace and Greenwich Borough
The future England international Wright was playing for semi-professional side Greenwich Borough for just £30 a week when he was scouted by Crystal Palace in 1985. Yet rather than give the non-league outfit some much-needed cash, the Eagles took a look around their training ground and decided to offer a set of weights to Borough in return for their incredibly talented young striker.
Wright went on to score 117 goals for the Eagles and was later voted the club’s Player of the Century. The whereabouts of the weights is unknown.
James Beattie + £7.5m for Kevin Davies
Blackburn and Southampton
A Blackburn academy graduate, Beattie only made four senior league appearances for Rovers before being shipped off to Southampton. The youngster was used as a makeweight in a deal which saw Davies, who cost the Lancastrians an additional £7.5m, move in the opposite direction.
Within a year both frontmen were employed at St Mary’s, with Southampton re-signing Davies following Blackburn’s relegation to the second tier. Beattie’s career on the south coast got off to a slow start, but he eventually became the team’s talisman before being sold to Everton in 2005.
Henrikh Mkhitaryan for Alexis Sanchez
Manchester United and Arsenal
Stop sniggering at the back there. There was a time when getting Sanchez for relative pittance would have been considered incredible business. Instead, he's now widely regarded as one of – if not the – worst signings in Premier League history.
And that's no exaggeration: the Chilean's on-pitch performances have been woeful, and his eye-watering contract a huge problem.
Mkhitaryan hasn’t exactly set the world alight in north London, but he’s not been a disaster either. By that measure, Arsenal are the clear victors here.
Lorik Cana + £1.8m for Fernando Muslera
Galatasaray and Lazio
Italian clubs like a swap deal more than most, but this time Lazio managed to persuade a foreign side to get involved. On the lookout for a new midfielder, the Rome-based outfit parted with £1.8m and goalkeeper Muslera to bring Cana to the Stadio Olimpico.
The former Sunderland man did well enough in Serie A, but Muslera’s longevity and honours list means Galatasaray got the better end of the bargain: the Uruguayan shot-stopper has racked up 327 appearances for the Lions, winning nine trophies along the way.
Andrea Pirlo for Andres Guglielminpietro + £1.7m
Inter and Milan
Oh dear, Inter. Pirlo’s first taste of life at San Siro came in blue and black rather than red and black, but the metronomic midfielder didn’t make much of an impression in his 22 Serie A outings for the Nerazzurri.
Milan had clearly seen something in those performances, though, and were only too happy to hand their neighbours Guglielminpietro and £1.7m in exchange for the Italian. Pirlo went on to win two league titles and two Champions Leagues with the Rossoneri, while Guglielminpietro (nicknamed Guly) played less than 50 games for Inter before being loaned to Bologna.
Jose Antonio Reyes for Julio Baptista
Arsenal and Real Madrid
Baptista memorably scored four times in Arsenal’s 6-3 defeat of Liverpool in the League Cup, but he only managed three Premier League goals during his season-long loan switch from Madrid. Arsene Wenger’s side finished fourth that year, a full 21 points behind champions Manchester United.
Fernando Torres for Alessio Cerci
Milan and Atletico Madrid
After reaching double figures for both goals and assists at Torino in 2013/14, Cerci moved to Atletico Madrid for €16m. Yet that dream move quickly turned into a nightmare, with the Italian winger making only six league appearances for the Colchoneros before being sent to Milan in exchange for Torres.
A return to Serie A didn’t bring about an upturn in fortunes, as Cerci scored just once in 33 games for the Rossoneri. Torres’ second spell at Atletico was much more successful, the striker finding the net 38 times across three and a half seasons.
