The Blues went to Stamford Bridge with some hope after a promising display against Manchester United, who could easily have won the three points after an unauthorized late kick from Dominic Calvert-Lewin.
Instead, Everton was sent back to Merseyside with his tail between his legs after a 4-0 loss to Chelsea.
It was the first time the boss had suffered such a heavy loss during his time at Goodison Park, but sadly, fans have seen too much this one quarter.
The investigation into how the Blues were beaten so easily continued for a few days after the match, before the effects of the coronavirus pandemic became the focus of attention.
However, with a return match against Liverpool on the horizon, thoughts are returning to how Everton could prepare to try to rectify what happened the last time.
And there aren’t a lot of clues in the past few months about the answer. The Blues participated in an intra-team friendly match at Goodison Park on Saturday, but only a few clips were broadcast of the session.
But, since the last time, it is clear that something must have changed.
After this defeat against Chelsea, Ancelotti said: “Everything went wrong.
“It is not difficult to judge this match, to analyze this match. We weren’t good enough defensively, too open, not compact. We lost a lot of duels and with the ball we made a lot of mistakes, with assists and so it’s not a good day. But what we can do is learn from our mistakes.
“Honestly, this is the first game we have not participated in. In the other games that we did not win, we competed until the end of the match. Today, it was wrong from the start. So we have to learn from the mistakes and learn for the next game. ”
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Who would have thought that the next match would be in more than three months?
But the boss is faced with some intriguing decisions to try to firmly put this defeat to bed, including one potentially surrounding his training.
During his stay at Goodison, the Italian apparently preferred to use a 4-4-2 system, presented to this team by Duncan Ferguson wisely after the dismissal of Marco Silva.
And, while it certainly produced good performances and made the most of Dominic Calvert-Lewin and Richarlison in particular, some weaknesses in the system were revealed by Chelsea in March.
Everton were overtaken in midfield by the hosts on this occasion, with young Billy Gilmour claiming high praise for his performance against the Ancelotti team.
The Blues reacted little to Chelsea’s dominance in this area, which led to the opening of many defensive holes.
The midfielder is certainly already an interesting debate, and injury issues in recent weeks have not made the situation much easier.
Fortunately, Ancelotti will have Andre Gomes available, but Fabian Delph remains in doubt – with Morgan Schneiderlin and Jean-Philippe Gbamin out of action.
Options are limited in this area, but even more so in central defense, with Michael Keane and Mason Holgate being the only senior options currently available.
And therefore, any potential opportunity to change things could be hampered.
Everton could easily line up a 4-4-2 for the upcoming derby – probably with Tom Davies and Andre Gomes filling the central roles in the midfield, with Gylfi Sigurdsson and Bernard potentially on the flanks.
Of course, there’s also the option of playing Djibril Sidibe in the right midfield, which could see Sigurdsson move to the center.
But could the boss be tempted by a change of system? Especially with Theo Walcott excluded for the next three weeks at least.
A return to 4-5-1 would give at least more body to the midfielder, and potentially leave less space for Liverpool to exploit as Chelsea did.
Or, perhaps, could we adopt a system of five in the back? Seamus Coleman would cover as the third central defender in this case, with Lucas Digne and Sidibe as the back.
Sure, these switches are possibilities, but against your rivals it will always be a gamble to make such a radical system change.
Ancelotti prefers a 4-4-2, calling it a “best defensive system” in the past – even if it didn’t seem like it was against Chelsea.
Much work has been done on the training ground since then under the most trying and difficult circumstances.
In the pressure environment of a Merseyside derby, can Everton finally ask a three-month question?