The Reds have never met Ludogorets and have only managed draws in their two previous meetings with Swiss side Basel.
However, it is against Madrid that Liverpool possess the best record, having won all three of their previous matches against the current European champions.
And, according to star striker Daniel Sturridge, Brendan Rodgers' side have themselves a 'saucy little draw.'
For one former Liverpool player, meanwhile, the draw presents a good opportunity for two reasons.
Indeed, Carragher, who won the Champions League with the Anfield side in 2005, thinks his former club have a 'decent chance' to get through and will also benefit from the experience of playing Spanish giants Real Madrid.
Great draw for Lfc decent chance to get through and the experience for the players of playing against Madrid.— Jamie Carragher (@Carra23) August 28, 2014
This season will be Rodgers' first ever in the Champions League as a manager, while many of Liverpool's players are also yet to taste European football.
Captain Steven Gerrard has, though, and was another member of their Europe-conquering squad of 2005. New signing Mario Balotelli is also a seasoned regular in the tournament.
After the draw, meanwhile, chief executive Ian Ayre said: "When I spoke to Brendan [after the draw], one of the things he said was 'The process starts now' - scouting and analysing them.
"We treat everyone the same - we take on every team with the same amount of effort and prepare in the same way."
Will Liverpool successfully negotiate their way out of Group B?