
Jose Mourinho, even as his stock has fallen, has always been a specialist cup manager. While his last few jobs have been less successful, he still took Tottenham to a League Cup final and Roma to a Conference League and Europa League final.
The Portuguese also has an impressive record in the Champions League. He won it, memorably, as a young coach at Porto, and then won it again with Inter in 2010. His Chelsea and Real Madrid teams often went deep into the competition, too.