1. Massimo Maccarone to Middlesbrough for £8.15m (2002)
A Teeside transfer record at the time, 18 goals in four years was by no means a rewarding return for chairman Steve Gibson. Massimo did manage some payback a few years on as he will be remembered largely for the brace he bagged in that astonishing Uefa Cup semi-final match against Steaua Bucharest.
2. Titus Bramble to Newcastle for £5m (2002)
Although arguably one of the buys of 2010 for Sunderland, Bramble’s performances for their Tyneside rivals were not quite as consistent. Nicknamed Titus Shambles buy Toon fans and neutrals alike, his awful howlers and overall clumsiness contributed to his downfall. Long sleeves on central defenders never helped anyone’s case either. I think it’s fair to say Titus is much happier these days!
3. Bruno Cheyrou to Liverpool for £2.5m (2002)
“The new Zidane.” Fear not, Gerrard Houllier was not going senile when he made this bold statement. He was merely wrong, very, very wrong. Cheyrou’s welcome was long outstayed when Liverpool offloaded the Frenchman back across the water to the pleasure of the Kopites.
4. Georgios Samaras to Manchester City for £6m (2006)
Another player that shone in Holland but flopped in England. Samaras’ transfer was greeted with joy and excitement by the City faithful. But weak, unconvincing performances and an ever diminishing goal record was enough to ship the player to Celtic, where he seems to have found his level once again.
5. Andriy Shevchenko to Chelsea for £30.8m (2006)
The biggest transfer flop ever? It’s certainly up there with the best of them. Sheva was a world star setting Serie A alight year after year. But he looked like a rabbit in the headlights upon signing for Chelsea. A rather inept rabbit at that! Nine goals in 47 games was an astonishing mismatch compared with his better than one-in-two record for Milan.
6. Zat Knight to Aston Villa for £3.5m (2007)
Dubbed Zat ‘Knightmare’ by many Villa fans, his move was doomed from the start as the defender found himself arrested on the night of his transfer in a drugs raid. At least they couldn’t doubt that he was now a Villain. Although Knight was not known for his garish mistakes, he found himself out of favour on more than one occasion due to the impressive performances of James Collins, Richard Dunne and Carlos Cuellar.
7. Robbie Keane to Liverpool for £18.3m (2008)
When Keane signed for his boyhood club, Liverpool, it looked like a match made in heaven. But a recipe combining Rafa’s lack of guile and Robbie’s lack of confidence ended up looking like something out of Hell’s Kitchen. Another Benitez flop as the Reds boss failed to get to grips with his buys from British clubs.
8. Jonathan Woodgate to Tottenham for £7m (2008)
Although what must seem like an improvement after a torrid time at Real Madrid, Woodgate’s time at Spurs has yet again been plagued by injury. There’s no doubting his class, but it is fair to say Daniel Levy wasted £8 million on this one.
9. Afonso Alves to Middlesbrough for £12.7m (2008)
Note to Premier League managers: as the list proves, just because a striker scores regularly in Holland doesn’t necessarily mean they will in England. The AA smashed Boro’s transfer record but the Brazilian flags and shirts donned by the Teesiders were not enough to spur this sorry Samba boy into life. Now something that the Championship club are sorely regretting!
10. Robinho to Manchester City for £32.5m (2008)
If there’s one thing we can thank Robinho for, it’s being very tired on September 1, 2008. His ongoing transfer saga kept us all awake on ‘deadline night’. The viewing was made all the more interesting by the fact he chose Manchester City over the then omnipotent Chelsea. On the pitch was not such compulsive viewing however. If only there were as many twists and turns in his performances as the tale itself.
That’s our list but we know for a fact there’s more honourable mentions due than Jonathan Woodgate’s had operations. So fire away…