Massimo Taibi, Venezia to Manchester United, £4.5m, August 1999
There were many attempts at Old Trafford to find a successor to Peter Schmeichel, but this was the most disastrous. Not exactly cheap, he lasted four months, his fate sealed when an innocuous shot from Southampton's Matt le Tissier dribbled pathetically between his legs and crawled over the line.
Sergei Rebrov, Dynamo Kiev to Tottenham Hotspur, £11.5m, June 2000
At Dynamo Kiev, he formed an outstanding partnership with Andrei Shevchenko, but once at Spurs, he seemed to lose the confidence of his managers and plummeted down the pecking order, before dropping off the radar entirely. Last heard of warning Spurs striker Roman Pavlyuchenko of the dangers of 'dark-skinned people', so perhaps we shouldn't mourn his failure.
Francis Jeffers, Everton to Arsenal, £8m, June 2001
Arsene Wenger is often cited as something of a mastermind in transfer dealing, but this may have been the point where he decided to concentrate on French youngsters. Jeffers was supposed to be Arsenal's "fox in the box", the man who cured them of their chronic desire to score beautiful goals. In the end, he was sold at a loss of over £5m.
Michael Owen, Real Madrid to Newcastle United, £16m, August 2005
Owen's dismay at signing for a club outside the top four seemed almost palpable and his injury record and clear desire to skedaddle as soon as possible mean that Newcastle have squandered a hefty (non-returnable) fee and a considerable sum in wages.
Jon Dahl Tomasson, Heerenveen to Newcastle United, £2.5m, July 1997
Tomasson was rather a forlorn figure at Newcastle (a recurring club in lists like this), but his success in Europe, even winning the Champions League with AC Milan in 2003, would suggest that the problem lay with the team rather than the player.
Bosko Balaban, Dynamo Zagreb to Aston Villa, £6m, August 2001
A mysterious one. A free-scoring forward in Croatia, he barely started a game for Villa and was passed out on loan as soon as was decent, with his contract cancelled at the end of 2003. After that, he joined Bruges, where he started scoring again.
Marco Boogers, Sparta Rotterdam to West Ham United, £1m, July 1995
His second appearance (as a substitute) earned him a red card against Manchester United, whereupon he promptly disappeared, turning up some months later in a Dutch caravan park. A free transfer swiftly followed, administered by a bewildered Harry Redknapp.
Ramon Vega, Cagliari to Tottenham Hotspur, £3.5m, January 1997
Oddly, Vega re-appeared on the radar as a possible owner of Portsmouth earlier this year so his work as an asset manager seems more successful than that in the centre of the Spurs defence where he became a byword for jittery indecision.
Faustino Asprilla, Parma to Newcastle United, £6.7m, February 1996
Asprilla (right) was supposed to be the final piece in a jigsaw for a title-winning Newcastle side. Instead, they began to unravel and were overhauled by Manchester United. Not all the Colombian's fault but the perception that he unbalanced the side was damaging to player and club.
Per Kroldrup, Udinese to Everton, £5m, June 2005
A mysterious one ? a substantial fee, followed by no desire to actually give him a game. Whatever failings he showed in training, they were significant enough for the club to offer him just the one appearance, before sending him on his way.
Juan Sebastian Veron, Lazio to Manchester United, £28.1m, July 2001; United to Chelsea, £15m, August 2003
The personification of gilding the lily. Supposed to be the final piece in the conquering jigsaw at Manchester United, he just didn't fit in to their midfield (and worse, in many eyes, pushed Paul Scholes out of position). Chelsea compounded the error by paying a second, smaller, fee for a player who's inability to adjust to English football was already obvious.
Stephane Guivarc'h, Auxerre to Newcastle United, £3.5m, June 1998
Signing the centre forward for the World Cup winners would surely be a success. Not at Newcastle who seemed not to notice that Guivarc'h failed to score for his country in their winning campaign. His non-goals-scoring touch didn't desert him at St James' Park either.
Adrian Mutu, Parma to Chelsea, £15.8m, August 2003
Proof that money guarantees nothing. The six goals in 27 games were unremarkable. His drug bust for cocaine use (and immediate sacking) were much more memorable.
The cheque books have been out during one of football's most expensive summers ever.
>> Click on the image to the right to launch our guide
The thing is, though – players don't automatically fit into teams and managers aren't infallible. There will be deals done in the next few weeks which will turn out comically bad. Almost as comical as some of these, the worst since the Premier League began in 1992.