5. Jose Mourinho
Jose Mourinho is one of the Most Successful Managers in Champions League History. He is regarded by a number of players, coaches, and commentators as one of the greatest and most successful managers in the world. In 2015 Mourinho was named the best Portuguese coach of the century by the Portuguese Football Federation (FPF). He returned to Porto in early 2002 as head coach, winning the Primeira Liga, Taça de Portugal, and UEFA Cup in 2003. In the next season, Mourinho guided the team to victory in the Supertaça Cândido de Oliveira, to the top of the league for a second time, and won the highest honour in European club football, the UEFA Champions League.
Mourinho moved to Chelsea the following year and won the Premier League title with a record 95 points, the club’s first league title in 50 years, and the League Cup in his first season. In his second year, Chelsea retained the Premier League and in 2006–07 he took the club to an FA Cup and League Cup double. Mourinho left Chelsea in September 2007, amidst reports of a rift with club owner Roman Abramovich. In 2008, Mourinho moved to Serie A club Internazionale. Within three months he had won his first Italian honour, the Supercoppa Italiana, and completed the season by winning the Serie A title.
In 2009–10, Inter became the first Italian club to win the treble of Serie A, Coppa Italia and the UEFA Champions League, also the first time Inter had won the latter competition since 1965. Beside Ernst Happel, Ottmar Hitzfeld, Jupp Heynckes and Carlo Ancelotti, Mourinho is one of only five coaches to have won the European Cup with two different teams. He won the first ever FIFA World Coach of the Year Award in 2010. He then signed with Real Madrid in 2010, winning the Copa del Rey in his first season.
The following year, he won the La Liga and became the fifth coach, after Tomislav Ivić, Ernst Happel, Giovanni Trapattoni and Eric Gerets, to have won league titles in at least four different countries: Portugal, England, Italy, and Spain. After leaving Madrid in June 2013, Mourinho returned to England to manage Chelsea for a second spell, during which they won another league championship.