Chelsea’s manager history in the past two decades – Part 2

This is Part 2 in a 4-part series. You can go back and read Part 1 here

Carlo Ancelotti: June 2009 to May 2011

Carlo Ancelotti’s first season at Chelsea was one that saw the Blues breaking records yet again.

Ancelotti’s reign began with a win when Chelsea faced Manchester United and won the FA Community Shield after a penalty shootout. Ancelotti’s team carried on this momentum, with six wins in the first six Premier League games of the 2009/10 season.

Ancelotti meant business, and he did not disappoint. Chelsea won the Premier League that season, with an impressive 27-5-6 record.

They broke the record of most goals scored in a season with 103 goals – a record that Manchester City later broke in the 2017/18 season by three more, with the record still standing to this day. However Chelsea still has the record for most goals scored at home in a season, with 68 goals.

Another upside to Ancelotti’s first season was that Chelsea won the FA Cup. This was the first time in the club’s history that Chelsea won the FA Cup consecutively. Chelsea had then become the seventh club to complete the double – Premier League and FA Cup in one season.

However, there were disappointments for the Blues that season. Despite going unbeaten in the Champions League group stage, Chelsea lost both legs of the round of 16 to Inter Milan, ending their European campaign early. The Blues also knocked out of the fifth round of the EFL Cup by Blackburn Rovers on penalties.

Ancelotti’s Chelsea went into the 2010/11 Premier League season as the defending champions with the task of retaining the title. It started off well for the Blues, with five consecutive wins at the start of the Premier League season.

Chelsea led the Premier League table for almost half the season. Unfortunately, a bad winter run helped Manchester United take their place at the top. From November to January, in the span of 13 games, they drew four times, losing five in that run. This slump had ultimately lost them the title. Chelsea finished second behind Manchester United in the Premier League with a deficit of nine points.

To add to their woes, Chelsea was knocked out of the UCL by United after losing both legs of the quarterfinals. The Blues were also knocked out of the EFL Cup by Newcastle United in the third round. A fourth-round replay in the FA Cup saw Chelsea lose to Everton on penalties.

After a disappointing end to their season, Ancelotti was sacked by Chelsea.

André Villas-Boas: June 2011 to March 2012

André Villas-Boas was appointed following the departure of Ancelotti. Villas-Boas’ first four months were off to a fairly good start. The Portuguese led the Blues to a 11-4-6 recrod across all competitions. Unfortunately, one of those losses was a loss against Liverpool in the EFL quarterfinals.

In Villas-Boas’ next 19 games, Chelsea went 8-7-4. The loss of points affected Chelsea’s league position, and after a 1-0 Premier League loss to West Brom, Villas-Boas was dropped by the club.

Roberto Di Matteo: March 2012 to November 2012

Former Chelsea midfielder Roberto Di Matteo was assistant manager at the time and stepped up as Interim Manager following the departure of Villas-Boas.

His time as interim is remembered as special, with the Italian’s focus on the cups proving to have been the right decision.

Shortly before Di Matteo stepped up, Chelsea had lost 3-1 to Napoli in the first leg of the UCL round of 16. The second leg would be Di Matteo’s third match as head coach, winning his first two. The second leg is still described as one of the best nights ever at Stamford Bridge, with Chelsea managing a 4-1 win, taking them through to the quarterfinals against all odds.

Chelsea beat Benfica and Barcelona on aggregate in the quarterfinals and semifinals, respectively. Robert Di Matteo saw the Blues to their first-ever Champions League title when they beat Bayern Munich on penalties in the final.

Di Matteo’s FA Cup run was successful too. He coached the Blues to win every game from their fifth-round replay all the way to the finals against Liverpool, which Chelsea won. By winning the FA Cup and Champions League, they had completed the Cup double.

Of the 11 Premier League games he was in charge of, he saw the Blues to 5 wins, 3 draws and 3 losses. Chelsea finished that season in sixth, their lowest league position finish since the 2001/02 season.

In June of 2012, Roberto Di Matteo signed a two-year contract, becoming Chelsea’s permanent manager following his successful interim spell.

In Di Matteo’s first three months in the 2012/13 season, Chelsea had 10 wins, 2 draws and 2 losses in all competitions. His next few games in charge, however, saw a dip in performance. Just one win in five matches put Chelsea in a difficult position. Most notably, Chelsea was on the verge of disqualification from the UCL group stage following a 3-0 loss to Juventus.

The loss to Juventus marked the end of Di Matteo’s reign as Chelsea manager.

Rafael Benitez: November 2012 to May 2013

Rafael Benitez was called up as Interim manager. The beginning of the Italian’s reign was off to a rough start with a pair of draws plus a defeat in his first three games in charge.

His fourth game in charge, however, was a great attempt at getting Chelsea to advance into the knockout phase of the UCL. Despite a dominant 6-1 win over Danish side Nordsjælland, Chelsea was unable to advance to the next round. Shakhtar Donetsk and the Blues were tied on points, but the Ukranian club was ranked ahead of Chelsea on head-to-head away goals. Chelsea finished third in the group, dropping to the UEFA Europa League.

In his 26 Premier League games, he coached Chelsea to a 15-6-5 record, allowing Chelsea to finish the season third.

Benitez also coached Chelsea all the way to the FA and EFL Cup semifinals where the Blues lost to Manchester City and Swansea City respectively.

On the brighter side of things, Benitez managed to acquire silverware for the Blues when they beat Benfica in the Europa League final.

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