Liverpool have lost a European game at home for the first time in six years after crashing out of the Champions League last-16 at the hands of Atletico Madrid.
With Wednesday's loss, Liverpool's run of 42 matches unbeaten at Anfield was broken, with the team's previous defeat at home coming to Chelsea in the Carabao Cup last season.
In addition, the result ended the Reds' winning streak at home in European competition, as Anfield was the site of a defeat for the first time since 2014.
The last time they crashed out at the last-16 stage of the competition was in 2006, when Benfica knocked them out – that was also the last time they lost both legs of a tie until Wednesday evening.
Klopp, meanwhile, saw his magic touch in knockout ties evaporate, as the manager lost his first two-legged tie since taking over in 2015.
During that stretch, Liverpool reached a Europa League final as well as two Champions League final, falling to Sevilla and Real Madrid in Klopp's first two final appearances.