Carlo Ancelotti
Another player on the list whose managerial career outshines his playing one. Carlo Ancelotti was a solid midfielder during his playing career. He started off at Parma before moving to AS Roma and finally to AC Milan where he officially called it a day in 1992 after persistent knee injuries.
Like Heynckes, Ancelotti has been in the world of football for a very long time. The Italian enjoyed 16 seasons as a player and is now in his 24th year as a manager. Ancelotti's playing days are best remembered for his time with AS Roma and AC Milan. The Italian was part of the Giallorossi side that won their second ever Scudetto in 1983 as well as the only Roma side to reach the final of the European Cup.
The Italian then moved to AC Milan where he played a pivotal role in ushering their dominance over the Serie A. The midfielder was part of the side that won back-back to European Cups, the last team to do so before Real Madrid. Persistent knee injuries saw Ancelotti retiring from the game at the age of 33, winning every major club titles available at the moment.
Ancelotti's managerial career started with the Italian national side as he worked as an assistant to his former AC Milan boss Arrigo Sacchi. Three years with the national team was soon followed by his entry into club management as Ancelloti took charge of Reggiana.
A single season with Reggiana was soon followed by a move to his boyhood club Parma which lasted just two years, as Ancelotti was given the sack due to poor results. Two seasons with Juventus was followed by a return to San Siro as Ancelotti made his way into the hot-seat of the club where he won everything.
During Ancelotti's time at the San Siro, AC Milan enjoyed one of their finest eras post-Sacchi as they reached three Champions League finals in eight seasons, winning two of them. Ancelotti also had domestic success as the Rossoneri won every footballing trophy on offer at the club level. Like Guardiola's Barcelona, Ancelotti's AC Milan team are believed by many to be one of the greatest club sides ever.
Ancelotti resigned from AC Milan in 2009 and made his way into English football by joining London giants Chelsea. Two seasons with the Blues was followed by another two with PSG and later, another two with Real Madrid before taking a year off from management. Ancelotti joined Bayern Munich after his one year break but was soon sacked after string poor results, succeeded later by Heynckes. The former Italian midfielder joined Napoli this season replacing Maurizio Sarri, who went to join Chelsea.
Ancelotti remains one of the seven men to win the Champions League as a player and as a manager. He also is one of two men to have managed a team in four Champions League finals. The Italian is also one of the three managers to win the Champions League titles three times.