Liverpool have been drawn in Group B of the UEFA Champions League along with holders Real Madrid, FC Basel and Ludogorets Razgrad.
The Reds were pitted against the holders of the competition in Thursday's draw in Monaco, and they'll also face trips to Switzerland and Bulgaria.
Madrid, who claimed their 10th European Cup with victory over city rivals Atletico in Lisbon earlier this year, last locked horns with Liverpool back in the 2008-09 campaign.
The teams met at the last 16 stage and after Yossi Benayoun's late header secured a famous 1-0 first-leg win at the Bernabeu, the Reds ran riot in the return at Anfield - powering to a 4-0 triumph in front of the Kop.
The only other competitive game between the teams came in the 1981 final in Paris when Alan Kennedy's goal sealed a 1-0 win for Bob Paisley's team.
Liverpool also have recent history with Basel after they were pitted against each other in the Champions League first group stage in 2002-03.
The first encounter ended in a 1-1 draw at Anfield, while the Reds came from three goals down at half-time to draw 3-3 at St-Jakob Park.
Basel have won the Swiss league title five times in a row.
Meanwhile, Liverpool have never faced Champions League newcomers Ludogorets Razgrad previously.
The Bulgarian title holders secured their place in the competition in incredible circumstances against Steaua Bucharest in the play-offs.
After trailing by a goal from the first leg in Romania, Wanderson netted a last-minute volley to force extra time in Razgrad.
However, they were reduced to 10 men when goalkeeper Vladislav Stoyanov was sent off in the 119th minute.
It meant centre-back Cosmin Moti was required to go in goal for the penalty shootout - and he emerged the hero, sensationally saving two spot kicks to ensure Ludogorets progressed 6-5 on penalties.
Stay tuned to Liverpoolfc.com for full details of the group schedule.