It was during the 2008-09 campaign when the 'Reds' last expereinced the knockout rounds of the European competition, having reached the final twice in 2005 and 2007. However since then, the club has invested heavily with little success.
A managerial merry-go-round saw Roy Hodgson, Kenny Dalglish and Brendan Rodgers try their luck at restoring Liverpool to its former glory, but it seems as if it needed a German to give that necessary edge.
The red half of Merseyside has blossomed under Jurgen Klopp, who took over in October 2015, continuing to offer a dangerous threat in the continent despite losing star man Philippe Coutinho to Barcelona in the latest transfer window.
They face Porto in their first leg on Wednesday, who are currently undefeated in the Portuguese national league and should not be overlooked. Liverpool have no excuse not to progress though, especially given the amount of money spent during their European hiatus.
Since that 2008-09 campaign, the 'Reds' have invested €861m in signings. A monumental investment that has reached its historic peak this season, spending €168m.
Many have not made a lasting impression at Anfield, however, with Mohamed Salah, Sadio Mane and Roberto Firmino firing on all cylinders, they now have a prolific attack that could do some damage to their Portuguese opposition.
If successful, the prize would be a place in the quarter-finals of the biggest club competition in Europe - their first time in a decade - as Klopp and his squad look to rise expections in Merseyside once again.