The self-proclaimed Special One is one of the best managers in the game and certainly one of the most consistently successful. The 51-year-old Portuguese coach returned to Stamford Bridge last July after six years away and remains the Blues’ most successful manager in the club’s history.
In his first spell in charge of the Blues, Mourinho won no less than six trophies in three years – two Premier League titles back-to-back, the FA Cup, two League Cup titles and the Community Shield.
He then moved on to Inter Milan in 2008, where he stayed for two years winning two Serie A titles back-to-back, the Coppa Italia, Supercoppa Italiana, and the Champions League before moving again to Real Madrid in 2010 where he won the La Liga title, Copa del Rey and Supercopa de Espana.
Even in his first position as head coach at FC Porto in his homeland, Mourinho won two back-to-back Primeira Liga titles in two years, as well as the Taca de Portugal, Supertaca Candido de Oliveira, the Champions League title and UEFA Cup.
What do all these spells and honours have in common? Mourinho has consistently won at least one trophy, predominantly a league title but not in Spain, in his first year in every job he has ever had so far.
Yet the Blues are now out of the FA Cup, the League Cup and have dropped off in the Premier League title in recent weeks – if Chelsea don’t win the Champions League, Mourinho will lose his record of always winning something in his first season at every club he has ever been in charge of.
If Chelsea win the Champions League this season, Mourinho breaks a record - becoming the first manager in history to win the competition with three different clubs - but if they don't Mourinho loses his record of always winning a trophy in the first year of his contract.