Both Reds manager Jurgen Klopp (55) and Blues coach Graham Potter (47) are under growing pressure as their teams continue to under perform.
While on paper they look like similar situations, there are some key differences facing the two managers, with both in desperate need of a good run of results as soon as possible.
Here, Flashscore take a look at the position each coach finds themselves in going into the match.
Form
Both Chelsea and Liverpool have been on a horrid run since the return of the Premier League following the World Cup, managing just five wins between them in all competitions from a combined 13 games.
The Blues in particular have suffered a lot of poor results, losing 2-1 to Fulham and scraping a 1-1 draw against relegation candidates Nottingham Forest.
Liverpool haven't fared much better - including a damning 3-0 defeat to Brighton and a shock 3-1 loss against Brentford.
Their poor run of results have brought on questions from fans and media alike with the futures of both managers coming into question.
Chelsea in particular have been poor since the arrival of Potter despite an initially promising start, and had the ruthless previous owner Roman Abramovich still been in charge, then he may well have been dismissed by now.
On the other side of things, Klopp was quick to squash any ideas of him leaving Anfield unless he was forced out.
Tenure
Where the situations for both managers begin to differ is in the long-term positions they find themselves in.
Potter was only appointed in September last year while Klopp has been on Merseyside since 2015 - a staggering near-eight year difference.
The loyalty the Reds hold towards Klopp sees his position far more secure than Potter's, with the German winning every major trophy during his tenure as Liverpool boss - including the club's first Premier League title.
However, the Chelsea manager has been in charge for just four months yet the sensible point of view would be for the Blues to bide their time with a clearly talented coach.
Despite this, their players have been performing to a poor standard for a while now and there are no signs of any shift or motivation from Potter, often making sweeping changes to the starting 11 and failing to find a settled team that brings results.
While neither club should be looking to replace their respective managers it has to be said that Klopp has the safety net of his previous success behind him if results don't change - whereas Potter needs to find a solution to his side's problems much faster.
As Chelsea have shown under new owner Todd Boehly, they have plenty of money to spend and it's hard to imagine they would find it hard to replace the Englishman if needed.
Transfer market
Talking of money, there are big differences between what the two clubs are spending in the transfer markets.
While the idea that Liverpool don't spend at all isn't necessarily true - they certainly spend a lot less than Chelsea.
The Blues have spent £460m since Boehly's arrival which includes five signings during January.
Youngsters David Datro Fofana and Andrey Santos have been brought in as well as three players ready for the first team in Benoit Badiashile, Mykhaylo Mudryk and Joao Felix (loan).
On top of that there are persistent links to further signings and it doesn't look like Boehly wants to slow down anytime soon - placing even more pressure on Potter to succeed.
So much money being spent gives Potter all the tools needed to succeed, meaning a change in results is more important than ever.
Klopp, on the other hand, has been open about the chances of Liverpool strengthening further after the arrival of Cody Gakpo - with supporters likely having to wait until the summer for further additions.
This again puts him in a different position to Potter with the German working from a slightly more limited position albeit with a strong starting set of players.
The match
Ahead of Saturday's game, it's safe to say that both managers are in troubling situations and need something to change quickly, particularly for Potter.
This is in part due to the reasons mentioned above but also down to the nature of Chelsea in the past and how quick they have been to replace even their most successful managers.
However, it would be rash for the Blues to act so quickly this time around and lose a coach who has been proven to succeed in the Premier League when given time.
With both sides so desperate for a win, it's shaping up to be a thoroughly entertaining fixture.
