Back in Serie A after nine years abroad and trophies with Bayern Munich, Real Madrid, Paris Saint-Germain and Chelsea, Carlo Ancelotti's is now set for an emotional reunion when his Napoli side host AC Milan on Saturday.
Ancelotti enjoyed great success at San Siro as a player and coach, but he returns to face a Rossoneri side largely forced to accept mid-table mediocrity in recent years, amid ownership changes and Juventus' domination.
Having won two European Cups and two Serie A titles plus three other trophies as a Milan player, Ancelotti then delivered a pair of Champions League crowns and the Scudetto in a trophy-laden eight-year spell in the dugout, which came to an end in 2009.
Ahead of Saturday's showdown at the San Paolo, we look at his finest achievements in northern Italy.
2002-03 CHAMPIONS LEAGUE
Ancelotti celebrated back-to-back European triumphs with Milan as a player in 1989 and 1990, and he translated that success into coaching. Boasting a star-studded side including Paolo Maldini, Rivaldo, Andriy Shevchenko, Filippo Inzaghi, Clarence Seedorf, Andrea Pirlo and Gennaro Gattuso, he guided Milan to Champions League glory at Juve's expense.
The Rossoneri finished third and 11 points adrift of Juve in Serie A that season but they got the better of them in Manchester, having beaten Bayern Munich and Real Madrid en route to the knockout phase before trumping Ajax and city rivals Inter.
Milan then headed to Old Trafford for an all-Italian showdown – the first time two teams from the same nation had met in the final of the continent's top competition – and became champions of Europe for the sixth time after outlasting Juve 3-2 in a penalty shoot-out following a tense goalless draw.
Ancelotti's men also won the Coppa Italia that season by beating his former team Roma over two legs in the final, before edging out Porto 1-0 in August's UEFA Super Cup.
2003-04 SERIE A
Milan boasted the same core of players the following season as they dethroned Juve in the league.
Shevchenko, who would go on to win the 2004 Ballon d'Or, scored 24 Serie A goals to lead Milan to their first Scudetto in five seasons, as Ancelotti and his team demonstrated their ability to sustain a title challenge.
Ancelotti once again relied heavily on the likes of Maldini, Shevchenko, Pirlo and Alessandro Nesta as his golden generation remained at their peak, but the Italian boss unearthed a new gem in Kaka. The Brazilian playmaker settled in seamlessly and dazzled in Milan, where he fast became a fan favourite.
Milan were knocked out of the Champions League in the quarter-finals that season, but it was still a strong campaign for the club as they finally enjoyed domestic success, thanks to Shevchenko and Kaka, the new rising star.
2006-07 CHAMPIONS LEAGUE
Redemption was on the minds of Ancelotti and Milan, and they got it against Liverpool in Athens.
Two years earlier, they endured a nightmare in Istanbul, where they infamously surrendered a 3-0 first-half lead in an incredible Champions League final defeat to the Rafael Benitez's Reds on penalties. It was a result that, understandably, left Ancelotti and Milan devastated.
"We had six minutes of madness in which we threw away the position we had reached until then," he said after the match, which was in Milan's control thanks to Hernan Crespo's brace on the cusp of half-time. "The match was well contested and it's inexplicable because the team played well for all 120 minutes. That's the way it went, and we must go forward. We recognise it, we are displeased and disappointed."
It was a bitter pill to swallow after losing their domestic crown to Juve, although that title was later stripped due to the Calciopoli scandal, which saw Milan start the 2006-07 season with an eight-point penalty. They promptly bounced back that term by conquering Liverpool and Europe.
There were no doubts about the result in the Greek capital, where Inzaghi's double avenged the heartbreak of 2005 and secured a 2-1 win. Milan went on to win the FIFA Club World Cup that year, beating Boca Juniors 4-2.
