After being handed a group stage draw from hell, the last 16 draw was no kinder for Liverpool, as they were pitted against German giants Bayern Munich.
History has also not been kind to Liverpool when they have faced the Bavarian club; having only beat them twice in seven matches. Likewise, Bayern will not welcome this draw, having only won once over that same period of time.
The most likely result between the sides is a draw, with the remaining four fixtures contested between them having seen them fixed in a tie. Therefore, away goals may prove crucial in the outcome of this match up.
In terms of progress in this year's edition of the Champions League, Liverpool will be confident, as they won through a tough group. However, one big concern will be their away form, having failed to win a single group stage contest away from Anfield.
Liverpool will have to try to win the tie in the first leg at Anfield, because on current away form in the competition, they will be fearing the worst if they need to get a result away at the Allianz Arena.
In contrast, German champions Bayern cruised through the group stage, picking up four wins and two draws from their six encounters.
While they may be faltering in the Bundesliga, with heavy speculation surrounding the tenure of coach Nikpo Kovac, the Germans have been their bulldozing best in European competition this season.
One large concern for 'Die Roten' is the potential absence of Thomas Müller. The forward was awarded a straight red card in the final group match with Ajax, for a wreckless high tackle, and thus could be ineligible to play either match against the Merseyside club.
The one thing that is for sure, the return of former Dortmund boss Jurgen Klopp to his native Germany, to face his old foes, is sure to produce one hell of a knockout tie.