Brendan Rodgers' side were drawn with Basel and Bulgarian newcomers Ludogorets in a generous group after a five-year Champions League hiatus. The Reds beat Real 5-0 on aggregate in the 2009 Champions League round-of-16 - the last time Liverpool reached the knockout stage of the tournament.
Liverpool will not appreciate reminders that Basel eliminated them from the first group stage in 2002, though, a match that signalled the beginning of the end of Gérard Houllier's Anfield era.
Yossi Benayoun scored Liverpool's winner at Real in 2009
Arsenal return to Borussia Dortmund, who they were beaten by, and beat, last season. The Gunners will also travel to the cauldron that is the Türk Telekom Arena, home to Galatasaray, as well as Anderlecht in a tricky Group D.
Chelsea were much more fortunate. They will enjoy Schalke's company again, there will be a Lisbon homecoming for José Mourinho at Sporting and Celtic's conquerors, Maribor, also lie in wait.
City drew Bayern Munich for the third season out of four and also face tough trips to Roma and CSKA Moscow.