Saturday's clash pits Red versus Blue for the 31st time in just the past eight seasons. Such familiarity inevitably breeds contempt, and the rivalry between the two sides has simmered for more than a decade, often boiling over on the biggest stages.
The two sides are geographically distant, but the friction is as much the result of what it represents; north versus south, Merseyside versus London, rich owner's versus rich history. Reds fans often tease their west London rivals' lack of history, but the Blues have been busy making up for lost time since Roman Abramovich moved into town.
Now Liverpool have the chance to complete a cup double, in the process wrecking Chelsea's hopes of a slightly more prestigious brace of their own.
Matches between the sides are often packed with incident, and this year's Wembley showpiece could be the latest in a long line of classic encounters. In anticipation of tomorrow's showdown, GiveMeFootball looks back at some of the best...
5. Liverpool 2-3 Chelsea aet - Carling Cup 2005
Jose Mourinho guided the Blues to their first trophy since the 2000 FA Cup victory over Aston Villa, overcoming Rafael Benitez in what was the first skirmish in an epic battle between the two managers.
Steven Gerrard's own goal ten minutes from time handed Mourinho's side a lifeline, which they duly took with both hands. Goals from the newly assembled strike partnership of Didier Drogba and Mateja Kezman secured the trophy, whilst 'the special one' was sent to the stands for taunting the Reds' fans.
The Portuguese boss watched the last 15 minutes on a dressing room monitor, but not even a late Antonio Nunez strike could halt the Chelsea juggernaut. Benitez and Mourinho were to lock horns on several occasions over the next few years, but it was the Special One who recorded the first blow here.
4. Chelsea 2-1 Liverpool - Premier League 2003
A Champions League qualification decider, which saw the Blues squeeze into fourth spot and Liverpool edged out for the first time since 2000. This game is also the rumoured reason why Abramovich plunged his fortune into the Stamford Bridge club the following season, so the tie had important consequences for both clubs.
Liverpool once again started the brighter, Sami Hyppia nodding them into an early lead. This was the pre-Abramovich, Claudio Ranieri era and goals from Eider Gudjohnsen and Marcel Desailly dragged the Blues back into the match.
The result meant that Liverpool were left to ponder UEFA Cup football, while for Chelsea it was beginning of a new dawn characterised by the limitless possibilities offered by the new Russian owner's chequebook. The Blues spent £120 million the following season and the trophies soon followed.
3. Chelsea 4-4 Liverpool - Champions League Quarter-Final, second-leg 2009
Liverpool came within a whisker of completing a comeback worthy of their 2005 Istanbul revival. 3-1 ahead from the first-leg, the Blues almost choked spectacularly on their own turf. Petr Cech was uncharacteristically dreadful, which made his defenders nervous and Chelsea were all over the place at the back. Even with the cushion of three away goals the Blues faithful looked on in horror as their side prepared to throw it all away.
Stamford Bridge was in crisis as the Reds raced into a 2-0 lead, Cech inexplicably allowing a Fabio Aurelio free-kick to squirm past. But this Chelsea side was a seasoned outfit, full of experienced Champions League campaigners. Here, it was left to Frank Lampard to pick up the pieces - John Terry was missing through suspension - and the England man turned in an inspirational two-goal performance to haul his side through.
The match finished 7-5 on aggregate in the London club's favour, one of the most exhilarating Champions League ties of all time.
2. Chelsea 1-2 Liverpool - FA Cup semi-final 2006
In the fifth and final meeting between the sides in the 2005-06 season, Liverpool finally came out on top.
By doing so the Reds ended Mourinho's hopes of a second domestic double, after victory in the Carling Cup and Premier League in the Portuguese coach's first season. By the time the two sides met at Old Trafford, the Stamford Bridge side were well on their way to wrapping up the league for the second consecutive year, but Mourinho was chasing his first taste of FA Cup glory.
Stunning goals from Luis Garcia - who was to prove the scourge of Mourinho's Chelsea - and John Arne Riise put the Reds 2-0 up before Drogba headed in to set up a tense finish. Joe Cole blazed over a great chance at the death but Liverpool dug in.
After the penalty drama in Istabul the previous season, Benetiz's side repeated the trick at the Millennium Stadium, dispatching West Ham on penalties and securing the Spanish manager's first domestic trophy in England.
1. Liverpool 1-0 Chelsea - Champions League semi-final, second leg 2005
Rarely is a 1-0 win so dramatic. In terms of controversy and significance this tie is almost unparalleled. Victory here was part of a magical Champions League campaign for the Reds, encompassing 'the' Gerrard strike against Olympiakos, memorable rearguard actions versus Juventus and the mother of all comebacks against Milan in the final.
A goalless first leg set up a cagey second at Anfield, but Luis Garcia's "ghost goal" in the fourth minute sent Liverpool through and Chelsea mad with frustration. Garcia insisted it was in, Chelsea, led by Terry, insisted it wasn't, but referee Lubos Michel pointed back towards the centre circle and the Reds celebrated.
In the wake of Liverpool's progress there were fervent calls for goal line technology, but seven years later the football world is still waiting. On the night, the Reds didn't care, withstanding heavy pressure for much of the match to earn a date with destiny in Istanbul. After a run to the final like theirs, victory over Milan three weeks later was just meant to be.