Since a 4-4 draw at Stamford Bridge in April 2009 in the quarter-finals the clubs have veered off in different orbits to such an extent that when they meet at Anfield on Sunday, Chelsea will boast a five-point lead in the Premier League while Liverpool are just glad to be out of the bottom three.
Scratchy wins at home to Blackburn Rovers and away to Bolton Wanderers represent a step forward for Roy Hodgson but Liverpool's wily manager will know more about his side's current health after the visit of Carlo Ancelotti's rampant side.
Likewise new owner John Henry will also get a first hand look at how much work, and investment, his new project needs before Liverpool can return to challenge for the title as they did two seasons ago under Rafael Benitez.
The problem for Hodgson is that, whatever Benitez claimed during a midweek rant, the squad he inherited was mediocre and he has so far had little financial muscle in the transfer market.
That may change in January but until then he must hope that Fernando Torres rediscovers some form and that Joe Cole, who is ruled out of Sunday's clash, begins to resemble the player he was at Chelsea.
With Dirk Kuyt injured, it was left to Maxi Rodriguez, a Benitez signing, to snatch the points at Bolton and Hodgson hopes that the Argentine will benefit from a run in the team.
"Maxi is a quiet man and his English isn't as good as some of the players, so it's not easy to have a long conversation with him," Hodgson told Liverpool's website.
"But he's picked up very quickly on what we want him to do and how we want him to play. In the games he's played recently he's been very good."
Chelsea will be buoyed by a 4-1 victory over Spartak Moscow on Wednesday that guaranteed their place in the last 16 of the Champions League.
John Terry and Michael Essien will be fresh for the trip to Merseyside having being rested against Spartak, although in-form Florent Malouda is out with an ankle knock.
TIGHTLY BUNCHED
Such is the small spread of points below the top three that were Liverpool to pull off a surprise win on Sunday they could suddenly find themselves on the fringes of the top four.
Manchester City are fourth behind Chelsea, Arsenal and Manchester United but suddenly look vulnerable after successive defeats - most worryingly a 2-1 reverse against Wolverhampton Wanderers last week.
City face sixth-placed West Bromwich Albion on Sunday when another defeat would leave their hopes of a serious title tilt in tatters and Roberto Mancini's future as coach in jeopardy.
Talk of dressing room unrest and player squabbles have helped create a sense of growing crisis at Eastlands and West Brom, who almost earned a point at Blackpool on Monday despite having two players sent off, will be keen to add to it.
Manchester United can close Chelsea's gap to two points when they host Wolves on Saturday although they will be hampered by injuries to Darren Fletcher and Nani.
"We've a couple of injuries. Nani has hurt his groin
