#4. Andriy Shevchenko – £30m
AC Milan to Chelsea in 2006
Undoubtedly, Mourinho's biggest failed transfer so far. Shevchenko was nearly 30-years-old when Chelsea signed him for such a hefty fee in 2006. He was on the club's sheets for three seasons while spending one season away on loan at Milan.
During his time in England, the Ukranian scored just 9 league goals in 57 appearances. However, his entire Chelsea career was not under Mourinho as the Portuguese was fired early on in the 2007/08 season.
#3. Victor Lindelof – £30.7m
SL Benfica to Manchester United in 2017
Manchester United's latest signing arrived from Benfica for £30.7m with a further £8.8m payable based on performance-based incentives. As things stand, he is only the third most expensive signing made by Mourinho.
It remains to be seen how well he will fit into the team, but Mourinho is usually spot on when it comes to his signings, especially the defensive ones.
Also Read: Rating Jose Mourinho's first season at Manchester United