Shevchenko 30.8 million

From 1999 to 2006, Andriy Shevchenko scored 127 goals in 208 games. No wonder Roman Abramovich wanted him. But Jose Mourinho didn't want to Ukrainian and the Portuguese Coach was fired not long after the $51 Million transfer was made. This was Chelsea's highest transfer fee (at that time) and the Blues hoped that their new signing would score copious amounts of goals.

In his two seasons at Chelsea, Shevchenko scored a lowly 22 goals (in 76 appearances). Apart from a good run of form at the end of 2007, Shevchenko was hugely disappointing with the Blues and never came close to living up to his transfer fee.