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#3 Roberto Di Matteo
The Italian’s time in the Chelsea hot seat lasted just five months, which was purely down to Abramovich’s ruthlessness, but what he accomplished in such a short span of time is nothing short of phenomenal. After excelling with the Blues as a player in the late 90s and early 00s, winning 2 FA Cups, 1 League Cup, 1 Charity Shield, 1 UEFA Cup and 1 UEFA Cup Winners’ Cup, Di Matteo returned to Chelsea as Andre Villas-Boas’ assistant in 2011.
The Italian inherited the Chelsea top job as caretaker after his boss’ sacking eight months later, with the club’s Champions League hopes in serious doubt following a 3-1 loss to Napoli under Villas-Boas. The events that followed are nothing short of Hollywood material. Di Matteo’s galvanised Chelsea proceeded to thrash Napoli 4-1 in the second leg, followed by incredible victories against Benfica and Barcelona in the quarters and semis, setting up a date with Bayern in the final.
Before the final with the German club, Di Matteo lifted his first trophy as Chelsea boss in the form of the FA Cup following an incredible 2-1 victory over Liverpool. If that was a surprise, no one could have predicted what came next. The date was May 19, 2012. The place, Allianz Arena. After two hotly contested halves, the Champions League final was pretty much anyone’s game following goals from Muller and Drogba for either side.
The match dragged on to extra time and could have very much gone Bayern’s way after Chelsea gave away a penalty, but Robben’s shot was saved by Cech. And then the unthinkable happened. Chelsea triumphed over Bayern on penalties, making them the first London club to lift the Champions League and Di Matteo the first Blues boss to win the prize.
The Italian was handed the job on a permanent basis a month later, and after some strong showings in the initial stages of the new season, was sacked when Chelsea’s form trailed off in England and Europe. The decision to sack Di Matteo after just eight months in charge caused widespread controversy amongst the fans, considering the phenomenal job he had done. Nevertheless, his status as a cult hero at Stamford Bridge was sealed, and he will go down as one of Chelsea’s greatest ever managers.
#2 Carlo Ancelotti
The legendary Italian manager was a massive hit at Stamford Bridge, where he proved just why he’s considered one of the all-time greats. Ancelotti, who was announced as the Blues’ new boss on June 1st 2009, won his first trophy barely two months later in the form of the Community Shield by beating reigning league champions Manchester United on penalties.
A string of brilliant performances followed, with Chelsea playing some terrific football under the Italian, who led them to the Premier League title in his debut season – with his team scoring 103 goals, becoming the first Premier League side to score 100+ goals in a single season.
An FA Cup triumph soon followed, with Chelsea securing their first ever domestic double under the Italian. The Blues started the following season strongly, but seemed to falter in the middle while crashing out in the quarter-finals of the Champions League at the hands of Manchester United. Despite leading Chelsea to a second place finish, Ancelotti was relieved of his position on the last day of the season following a 1-0 loss to Everton.
Apart from getting Drogba firing on all cylinders, Ancelotti left Chelsea with the third-highest win percentage in Premier League history – a record surpassed only by Jose Mourinho and Sir Alex Ferguson. All in all, it’s safe to say that the Blues and their flamboyant owner parted ways with the Italian too soon.
#1 Jose Mourinho
Did you REALLY expect anyone else to be on the top of this list?
The charismatic Portuguese proved that he had the cunning to match those immortal words “We have top players and, sorry if I’m arrogant, we have a top manager. Please don’t call me arrogant, but I’m European champion and I think I’m a special one”.
Jose Mourinho was snapped up by Chelsea after leading Porto to an unprecedented double in 2004 – including a Champions League that they won in the most dramatic of circumstances. It didn’t take long for his success to follow him to the shores of England, with Chelsea lifting the domestic double in Mourinho’s first season while setting the record for most Premier League points as well as the fewest goals conceded. The following season started equally well for Mourinho and Chelsea, who went on to lift the Community Shield before winning their second consecutive Premier League title.
The 2006-07 season was disappointing by Mourinho’s standards, but he still managed to lift the FA Cup and League Cup – thus winning every domestic title possible for an English top-flight manager. The Portuguese tactician departed Chelsea unexpectedly in September 2007 following differences with owner Roman Abramovich, but not before sealing his status as the Blues’ greatest ever manager.
Mourinho returned for a second spell at Chelsea in 2013 and lifted the Premier League and League Cup in his second season while overseeing some terrific football before once again departing in 2015 by ‘mutual consent’.
The manager has since been at Manchester United and current club Tottenham with varying degrees of success, but the club Mourinho will always be associated with – not least because of his nickname – is Chelsea. The love affair the Blues have with the Portuguese is just incredible. Somewhere deep, deep down – both of them know that it isn’t quite over yet.
