2008-09: Standard Liege
Having made serene progress past Toulouse in 2007, Liverpool went back to doing things the hard way against Standard Liege 12 months later.
The Reds escaped with a 0-0 draw from the first leg in Belgium - thanks in the main to Pepe Reina’s first-half penalty save - and were on the brink of facing a shootout to decide the outcome of this third qualifying round tie at Anfield a fortnight later.
Step forward Dirk Kuyt.
So often the man for the big occasion, the Dutchman netted in the 118th minute to secure a 1-0 aggregate victory and a place in the group stages.
A clash with Chelsea again proved to be Liverpool’s undoing in the competition proper, though, with the London club coming out on top in a thrilling quarter-final that finished 7-5 on aggregate.