Jurgen Klopp has come a long way since his first European match but as he prepares to mark his 100th as a reigning Champions League winner the journey has given him plenty to reflect on.
Klopp made his European managerial debut in charge of Mainz against FC Mika in Ashtarak, Armenia, in July 2005, having earned their UEFA Cup spot via a Fair Play place.
The small Bundesliga club also beat Iceland's Keflavik before losing to eventual winners Sevilla in the first round proper.
"It was not that we didn't want to win but it was difficult to create this very special atmosphere in the league: once we got through the group and into the knockout stage it was clear it was all or nothing.
"In the league it was, 'if we win we can be seventh and if we lose we will be ninth' so there was nothing we could really win in the league season and that's why the two finals (they also lost the League Cup) were probably the stand-out moments of that season.
"The years after, in the Champions League, we didn't really think we could go to the final but we knew from the start there was probably 10 clubs that could go to the final and we were one of them and we should give it a try.
"Europe has been special for us so far and hopefully it will stay like this forever."
Victory over Napoli – or Red Bull Salzburg's failure to beat Genk – will see Liverpool qualify for the knockout stage with a match to spare and give Klopp the chance to rest players for the final game next month.
"Unfortunately I'm not too good at thinking about games we have next week or in two weeks. The team selection is about winning this game, nothing else," he said.