Date: 1st March 2019 at 6:49am
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We return in 2009, now six years into ’s Chelsea reign. Having sacked Scolari for a poor run of form and an unhappy dressing room, Chelsea turned to a recent winner of the Champions League and the first of three Italian permanent managers of Abramovich’s Chelsea.

Having been humiliated by Liverpool in the 2005 Champions League final, Ancelotti’s AC Milan returned to the final two years later, avenging that defeat to win 3-0.

Ancelotti’s AC Milan side were widely regarded as one of the best European sides and their success led Abramovich to arrange one of his famous yacht visits.

This season also marked a noted difference in Chelsea’s transfer activity, spending just £23 million pounds on Ross Turnbull, Daniel Sturridge, Yuri Zhirkov and Nemanja Matic.

Of course the squad was already strong, but the club had chosen not to strengthen with any key signings.

This however didn’t phase Ancelotti, his free flowing attacking side broke records, including most goals scored in a season (103), most goals scored at home (68) and best goal difference (+71).

Ancelotti became the first Chelsea Manager to win the double, lifting the FA Cup with a 1-0 win over Portsmouth, to go alongside the Premier League title they won by a point ahead of Manchester United.

Despite the attacking and the double win, there was one black mark on Ancelotti’s season.

In the round of 16 in the Champions League, Chelsea were knocked out by Inter Milan, who would later go on to win the competition managed by one Jose Mourinho.

Ancelotti’s second season failed to provide the same success as the first. Assistant manager was suddenly sacked, January signing and Chelsea’s most expensive player failed to settle and hit the heights he had at Liverpool.

Chelsea came second in the league, were knocked out of the Champions League by Manchester United and we’re knocked out of both domestic cups in the early stages.

In Abramovich’s most ruthless moment, Ancelotti was sacked in the tunnel at Goodison Park after the final game of the season.

Win percentage: 69.47%

Games managed: 109

Being no closer to winning the Champions League, Abramovich called for a drastic change. In came one of Europe’s hottest young coaches, fresh on the back of completing the treble with Porto.

34-year-old Andre Villas-Boas had worked for Chelsea before as part of Jose Mourinho’s backroom staff.

He proved his knowledge of the game becoming the youngest coach to win a European trophy when he won the UEFA Cup in 2010.

Villas-Boas came with a remit of phasing out some of the older members of the squad and creating a young exciting side, able to finally win the Champions League.

The young coach employed a high line defence which exposed ’s biggest flaw (his lack of pace), dropped completely and fell out with other key players.

Being no stranger to sacking managers due to the influence of his key players, Abramovich ended the Villas-Boas experiment after a first leg 3-1 defeat to Napoli, in which Frank Lampard, and we’re left on the bench and a 1-0 defeat to West Brom that left the club battling Arsenal for 4th place.

Villas-Boas was replaced by his assistant manager and the rest they say, is history.

Win percentage: 47.5%

Games managed: 40

Roberto Di Matteo

The greatest night in the clubs history, which saw Chelsea win the Champions League, forced Abramovich to hand the managers job to Di Matteo on a full time basis.

However, the team failed to hit the heights of the year before.

A big squad overhaul, including losing Didier Drogba and signing Eden Hazard, saw Di Matteo out of his depth.

The team struggled again and following a run of four games without a win and a 3-0 defeat to Juventus in the Champions League saw Di Matteo’s spell as manager came to end after 262 days.

He was replaced by Rafael Benitez for the rest of the season. The club went on to win the Europa League having been the first Champions League winner to be knocked out in the group stage the following season.

Win percentage: 57.14%

Games managed: 42

*this figure includes the games as caretaker manager.

To be continued…