10. Juan Cuadrado (Fiorentina to Chelsea £23.3m, 2015)
Cuadrado looked like an astute addition in 2015, but the Colombia international was never able to replicate his exhilarating Serie A displays in the Premier League.
That he found game time hard to come by clearly didn’t aid his efforts to hit the ground running, but the former Fiorentina man still didn’t do enough in his occasional appearances to earn an extended stay at Stamford Bridge. After two years on loan at Juventus, he finally signed permanently for the Old Lady in summer 2017 for €20m.
9. Jean Makoun (Lyon to Aston Villa £6.2m, 2011)
“I've left a very good club in Lyon, a side which has played Champions League football, but I’m very excited by this new challenge at Aston Villa,” Makoun said after his move to England.
He probably regretted his decision after just a couple of weeks: the midfielder was stunned to learn that a red card in his fourth Premier League appearance against Blackpool brought with it a three-game suspension, and his Villa career came to a premature end after subsequent showings against Wolves, Everton, Newcastle and Hereford. Just the £564,000 per appearance, then – and that's not even including his wages.
8. Jean-Alain Boumsong (Rangers to Newcastle £8m, 2005)
This was a strange signing on many levels, with Newcastle paying Rangers £8m for Boumsong’s services just a few months after he’d been available on a free.
The 27-time France international actually started his career at St James’ Park well, before basic defensive errors began to creep into his game and adversely affect Newcastle’s results. Juventus, having been relegated to Serie B just a few months previously, took Boumsong off the Magpies’ hands in August 2006 – though he never featured in Serie A once the Old Lady made it back.
7. Benni McCarthy (Blackburn to West Ham £2.25m, 2010)
Another disappointing winter acquisition for the Hammers. McCarthy arrived in east London in pretty poor form, with 14 top-flight outings for Blackburn in the first half of the season having yielded just one goal.
Gianfranco Zola’s side were in desperate need of some additional firepower as they attempted to pull themselves clear of the relegation zone, but the South African wasn’t the man to provide it: after 14 appearances and zero goals in all competitions, McCarthy left the club with a £1.5m pay-off in April 2011.
6. Chris Samba (Anzhi Makhachkala to QPR £12.5m, 2013)
Harry Redknapp considered Samba the perfect man to shore up Rangers’ leaky backline in 2012/13, talking him up as a “proper centre-half” and “just what we need” after a £12.5m deal (on £100,000-per-week wages, obviously) was sewn up on deadline day. Only weeks earlier, Redknapp had declared that "you shouldn't be paying massive wages when you've got a stadium that holds 18,000 people".
Things didn’t work out as planned, though, for manager, club or player: Redknapp resigned days later, QPR were later relegated and Samba – who told fans to "get over" the fact he was paid so much at Loftus Road – was forced to go crawling back to Anzhi in the summer.
5. Afonso Alves (Heerenveen to Middlesbrough £12.5m, 2008)
Tottenham fans are well aware of the pitfalls associated with signing strikers from the Eredivisie, with Vincent Janssen having joined a much-maligned list that includes Jozy Altidore, Siem de Jong and Mateja Kezman rather than Luis Suarez, Ruud van Nistelrooy and Robin van Persie.
Afonso Alves was another member of the former group: despite finding the net six times in his first 11 Premier League appearances, the Brazilian quickly faded and was sold to Al-Sadd following Boro’s relegation in 2009. Still, he'll always be remembered for his hat-trick in that 8-1 tonking of Manchester City.
4. Guido Carrillo (Monaco to Southampton £19.1m, 2018)
Having £75m burning a hole in your pocket can do strange things to a football club. After selling Virgil van Dijk to Liverpool, relegation-haunted Southampton fancied a statement signing to show fans they were still ambitious – that, and attempting to avoid the drop having averaged only a goal per game under Mauricio Pellegrino by the end of January.
It turned out that Carrillo was not the answer. A big-money signing who'd helped Monaco to the Ligue 1 title in 2016/17, the Argentine striker – known to Pellegrino from their days together at Estudiantes – ultimately started just seven games (five in the league) and never scored for the Saints as they narrowly survived. Incoming manager Mark Hughes played him just twice from mid-March, and he was farmed out on loan to Leganes that summer.
3. Kostas Mitroglou (Olympiakos to Fulham £12.4m, 2014)
There’s putting all of your eggs in one basket, and then there’s Fulham signing Mitroglou for a club-record fee in January 2014. Granted, the Cottagers did also bring in Johnny Heitinga and Lewis Holtby on deadline day, but Olympiakos’s prolific marksman was identified as the player who could score the goals to keep Rene Meulensteen’s men in the Premier League.
Except he couldn’t. Unfancied by Meulensteen’s successor Felix Magath, Mitroglou started just one game in English football as the Cottagers fell through the top-flight trapdoor.
2. Fernando Torres (Liverpool to Chelsea £50m, 2011) and Andy Carroll (Newcastle to Liverpool £35m, 2011)
There were already signs that Torres was on the wane when he swapped Anfield for Stamford Bridge at the start of 2011, but Chelsea learned the hard way; £50m bought just 20 Premier League goals across three-and-half seasons, and gave Liverpool fans the chance to gloat.
Or at least it would have done had the Reds not spent most of the proceeds on Andy Carroll, who managed 11 goals in 58 appearances and looked entirely unsuited to the Reds’ style of play throughout his miserable 18 months on Merseyside. Not that it stopped Brendan Rodgers from signing Mario Balotelli three-and-a-half years later...
1. Savio Nsereko (Brescia to West Ham £9m, 2009)
Now 29, Savio’s last five clubs have been Atyrau (Kazakhstan), Lietava Jonava (Lithuania), Beroe Stara Zagora (Bulgaria), Pipinsried (Germany) and Vereya (Bulgaria), which probably says more about his true level of ability than 2009’s £9m move to West Ham – easily one of the most bizarre transfers in Premier League history.
The Irons handed the former Germany U20 international their No.10 shirt at Upton Park, but he failed to make an impact and enjoyed just a single Premier League start (he appeared in nine other games from the bench) before being shipped off to Fiorentina seven months later.
Karren Brady later investigated the deal upon her arrival at West Ham, but her findings were never made public.