10 Most Expensive Transfer Flops In Premier League History

8. Sergei Rebrov

Rebrov had been fantastic during his time with Dynamo Kiev in the late 1990s, forming a devastating strike partnership with Andriy Shevchenko. When George Graham signed him for Tottenham in May 2000, it was seen as an extremely shrewd piece of business. Almost immediately, however, the former Ukraine international was a shadow of the player many expected to see grace the English game. He managed just nine league goals in his first season at White Hart Lane, which considering he was expected to be a lethal marksman, was a very disappointing return. When Glenn Hoddle replaced Graham in 2001, it was clear that the ex-England manager didn't rate him. The 2001/02 season was an abysmal one for Rebrov. He scored just one Premier League goal in 30 appearances, and everyone associated with Spurs had seen enough. He was sold to Fenerbahce in 2002, and must go down as one of the most disappointing signings in the club's history.