The two match-ups between the sides in Group G were notable only for the usual dour, defensive qualities on display as both legs failed to conjure up a goal.
Liverpool topped the group by a point from their domestic rivals but both were knocked out in the First Qualifying Round that followed.
Chelsea were humbled 3-2 on aggregate by Barcelona while the Reds suffered humiliation at the hands of Benfica, going down 3-0 over the two legs.
2006-07
Semi-finals: Chelsea 1 Liverpool 1 (1-4 pens); First leg: 1-0 Chelsea, 2nd leg: 0-1 Liverpool
Chelsea suffered heartbreak again at the hands of their rivals, this time missing out on the final after a woeful penalty shoot-out.
A goal from Joe Cole won the first leg for Chelsea but Daniel Agger hit back in the return fixture for Liverpool.
Arjen Robben and Geremi missed their spot-kicks to send Anfield into delirium.
2007-08
Semi-finals: Liverpool 3-4 Chelsea (aet) First leg: 1-1; Second leg: Chelsea 3-2
The teams were drawn against each other in last season's semi-finals and at last provided fans with some decent goal action and Chelsea with a rare success.
The luck seemed to be on Chelsea's side this time as a stoppage-time own goal from John-Arne Riise cancelled out Dirk Kuyt's strike and gave them a 1-1 first leg draw to take back to Stamford Bridge.
In complete contrast to their previous clashes, both sides went for the jugular in the second match and the result was an enthralling contest settled after extra-time.
A double from Didier Drogba and a Frank Lampard penalty proved enough to hold off a late Liverpool fightback.
Premier League: Chelsea 0 Liverpool 1; Liverpool 2 Chelsea 0
Finally, it is the Reds who have come out on top in their league encounters this season.
Not content with ending Chelsea's proud 86-game unbeaten home record courtesy of an early Xabi Alonso goal, they performed the same trick in October.
In a game packed full of drama, a tight game was turned on its head by the harsh sending-off of Blues midfielder Frank Lampard for a tussle with Alonso on the hour mark.
Despite hanging on well with 10 men, a late double from Fernando Torres broke the Londoners resistance and ensured victory for a resurgent Reds side.
