Virgil van Dijk's injury prompted fears their campaign would fall apart, but six wins out of nine top-flight matches since his ACL blow gave manager Jurgen Klopp hope that his side could survive without the colossal Dutchman.
What happened next, however, proved to be a nightmare of epic proportions - and one that ultimately saw their hopes of retaining their title diminished.
Two more long-term injuries to Joe Gomez and Joel Matip propelled the Reds into a fully brown crisis in defence.
Natural midfielders Jordan Henderson and Fabinho were forced to partner up at the back, before Ozan Kabak and Ben Davies were signed as emergency recruits in January.
There was also notable absentees in midfield with Thiago Alcantara, Henderson and Fabinho later picking up injuries.
Diogo Jota, who who had dazzled at the start of the campaign following his £40m move from Wolves, was also sidelined for a six-week period.
The injuries saw a quite remarkable drop off in form from the then-Premier League champions.
After a 7-0 win over Crystal Palace in December, they went on to win just three out of 14 matches, which included an extraordinary run of six consecutive defeats at Anfield - a disastrous run of form at home that had not been seen before in the club's history.
The six consecutive defeats have come in the space of just 46 days, starting with a 2-1 loss against Burnley, then Brighton (1-0), Manchester City (4-1), Everton (2-0), Chelsea (1-0) and Fulham (1-0).
This season, Thomas Tuchel's Chelsea seem to be suffering an eerily similar fate.
Just like Van Dijk for Liverpool, Chilwell's ACL injury has been the catalyst for a big influx of arrivals in Cobham's medical room.
After a superb start to the campaign, the injuries have started to coincide with a rocky patch of form for the European champions.
They drew with an out-of-sorts Manchester United, were extremely lucky to beat Watford and were defeated by West Ham last time out, which saw them drop to third in the table.
Their midfield situation, to put it lightly, is dire.
The Blues have just two fully fit central midfielders in Ruben Loftus-Cheek and Saul, who was signed on loan during the summer but has had two nightmare appearances which has led to him being hooked off at half-time.
Ross Barkley can also play in the middle, but he is more accustomed to an attacking role and doesn't fit the holding role as one of the two midfielders in Tuchel's 3-4-3 system.
When your luck's out, it's really out - as Liverpool found out last season - and the situation regarding Mateo Kovacic is proof of that.
The Croat returned to Chelsea training on Monday after hamstring trouble, only to return a positive coronavirus test on Tuesday.
He had been out of action since late October and Blues boss Tuchel had hoped to ease him back in this week.
N'Golo Kante remains sidelined with a knee issue, while Jorginho has been forced to play through the pain of a back niggle and will now miss Wednesday's Champions League trip to Zenit.
Kovacic, Kante and Jorginho are all vital to Tuchel's system as Chelsea's stellar defensive midfielders, and the Blues have battled to offset their respective absences.
The problems are not just at the back, either.
Marcos Alonso picked up a knock in the defeat to West Ham last weekend, while Trevoh Chalobah and Ben Chilwell are still out.
Ross Barkley may well have a big part to play for Chelsea, whose incredible squad depth has been diminished in quite remarkable fashion in recent weeks.
Tuchel, however, will be hoping his largely unscathed attack can do the business for him.
Havertz, Romelu Lukaku, Timo Werner, Christian Pulisic, Hakim Ziyech, Mason Mount and Callum Hudson-Odoi are all fully fit.
So now more than ever, the Blues need their attackers to find their rhythm, with games coming thick and fast over the Christmas period and starting with a Champions League clash against Zenit on Wednesday.