The draw for the UEFA Europa League Round of 32 was held in Nyon, Switzerland on Thursday, and Liverpool discovered that they will need to make the long trip east to Russia in February to face Zenit St. Petersburg.
Draws for the first two knockout stages, in fact, both gave the Reds potential long-distance trips.
Should Liverpool overcome Zenit, they will face the winners of the Basel vs. Dnipro Dnipropetrovsk tie in the Round of 16—meaning a possible trip to Ukraine to go alongside their visits to Anzhi (from the group stage) and Zenit.
Here is your definitive guide to the Reds' opponents for the last 32, including how Liverpool might look to defeat the Russians when they clash in February.
Zenit St. Petersburg are the current Russian Premier League title holders. In fact, they've won the last two domestic league campaigns and have not ended the season outside the top three since 2008. They were also the winners of the Europa League itself in 2007-08.
A major player in the increasingly strong Russian game, Zenit are owned by Gazprom, the Russian petroleum company that is one of the biggest companies in the world. Needless to say, their spending power is therefore rivalled by few.
Even so, they have not yet managed to make a big impact in the Champions League, failing to ever reach the quarterfinals.
They have been in the media recently as a result of one of their fan groups releasing a statement demanding that no non-white nor homosexual players be considered for selection for the team—something which the club has flat out refused to consider.
Despite their consecutive domestic league titles, Zenit are not in the best position this season to retain their trophy.
Zenit currently lie in third place, having lost three of their 19 matches to date. They are five points off the pace at present and will not resume their season until after the lengthy winter break; the next fixture is in early March against Lokomotiv Moscow.
This means that the two legs of the Round of 32 will be played before Zenit resume league action.
They ended the first half of the campaign with a 1-1 draw at home to CSKA, a 4-2 win at Spartak Moscow and another 1-1 draw, this time at home to Anzhi.
Zenit are actually one of the eight teams who dropped out of the UEFA Champions League by finishing third place in their group stage.
They went up in Group C against Malaga, AC Milan and Anderlecht but after winning just one of their three home games failed to keep pace with the Spanish and Italian sides.
A 1-0 win in the final match in Milan was the highlight of the group stage for the Russians, but it was already too late to catch up with the Italians.
That win brought them their only goal scored away from home, netted by Danny.
Seven points from their six games was not enough for Zenit to be one of the four best third-placed teams, which would have seen them seeded for the Europa League draw.
Zenit had hoped that the duo would aid progress in the Champions League. However, the Brazilian forward has only managed to add two goals in the league and a further one in Europe amid reports of battles with his manager.
Key midfielder Igor Denisov has also had his problems with the big-money duo, criticising the high wages they were earning and being forced to train with the club's younger players until he apologised.
Plenty of the Russian national team also ply their trade with Zenit, including goalkeeper Vyacheslav Malafeev, full-back Aleksandr Anyukov, midfielder Roman Shirokov and striker Aleksandr Kerzhakov.
Portuguese stars Bruno Alves and Danny are also key components of a very strong team.
It's going to be tough for Liverpool, no doubt about it.
Zenit might not have made their mark in the Champions League this season the way they would have wanted, but they are packed full of quality players and have plenty of experience in European competition. Infighting and uncertainty over the manager are a problem; whether that is still the case in February remains to be seen.
Liverpool will not be overly impressed with having to make a round trip of around 4,000 miles into the Russian winter. Brendan Rodgers may decide, league form depending, to send another shadow side.
The Reds will fancy their chances of getting a result in the second leg at Anfield so will hope to remain in the tie, perhaps with a draw or at least scoring an away goal, after the first leg.
This could turn out to be one of the ties of the round. It certainly gives Liverpool a tough assignment in their path towards the trophy, but the Reds know anyway that they will have to beat tough opponents to achieve that objective.
The Europa League lies ahead, though for now Rodgers and his team will be focusing on the busy Christmas period and trying to improve the squad in the January transfer window.