Top 5 Biggest Transfer Flops

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With Europe’s top clubs splashing the cash this summer on the likes of James Rodriguez, Toni Kroos and Luis Suarez there’s bound to be a few duds amongst the transfer hits.

We look at some of the worst deals involving foreign clubs, on a par with the likes of Fernando Torres and Andrei Shevchenko to Chelsea.


Spanish Soccer - Primera Division - Real Madrid v Real Betis

Denilson’s record transfer is a cautionary tale to all clubs considering signing a player based on their form at an international tournament.

The Brazilian sparkled at La Tournoi in 1997 and unfashionable Real Betis surprised rivals by smashing the world transfer record for him a year later.

His signature was supposed to inspire the Andalusians to compete at the top of La Liga but the club were relegated in his second season with minimal impact from Denilson.

After failing to live up to his price tag, the winger wound down his career at a succession of obscure clubs in America, Saudi Arabia, Vietnam and Greece.

Gianluigi Lentini


The football world was shocked in 1992 when AC Milan broke the world transfer record, splashing out £13 million for Torino winger Gianluigi Lentini.

The pontifical world wasn’t too impressed either, with Pope John Paul II condemning the exorbitant fee as “’an offence against the dignity of work”.

While allegations surfaced of illicit payments involved in the transfer, Lentini set about repaying his huge fee with several goals and assists in his first season.

However his time at Milan, and career elsewhere, was never the same after a near-fatal car crash in 1993.

He played for several more Serie A clubs, including a return to Torino, but could never reproduce the form that persuaded Milan to break the world transfer record for him.

Dmytro Chygrynskiy

Spain Soccer Barcelona Chygrynskiy

Despite his undoubted managerial genius, Pep Guardiola’s transfer record at Barcelona was questionable to say the least.

Top of the flops was Ukrainian centre-back Dmytro Chygrynskiy, who Guardiola paid over £20 million for in 2009.

Barca also signed Zlatan Ibrahimovic around the same time and, while he flopped at the Nou Camp, it was more to do with Guardiola’s handling of him than the striker’s mercurial talents.

However, Chygrynskiy was a different matter altogether. The defender signed for five years but lasted just one, jettisoned back to Shakhtar Donetsk after just twelve disastrous appearances for the Catalans.

Elvir Baljic


Elvir Baljic isn’t a name easily recalled by football fans and is best forgotten by Real Madrid supporters. He was signed by John Toshack for over £20 million but injuries and poor form littered his career at Madrid.

He made just 11 appearances, seven from the bench, during his solitary season at Real, before being sent back on loan to Fenerbahce and eventually offloaded to Galatasary.

The Bosnian striker was voted Madrid’s second-worst signing every by readers of Marca – runner-up to Jonathan Woodgate.

Gaizka Mendieta

Soccer - UEFA Champions League - Group D - Lazio v Nantes

The Spanish midfielder was one of the most sought-after players on the planet after leading Valencia to consecutive Champions League finals and being named European Midfielder of the Year in 2000 and 2001.

Therefore, it was no surprise when Lazio made him the sixth most expensive player of all-time with a £30 million move to Rome.

However, Italian football did not suit the stylish midfielder and he was sent on loan to Barcelona after just one term at Stadio Olimpico before ending up at Middlesborough.