Liverpool relinquished their grip on the Champions League after a costly goalkeeping error enabled Atletico Madrid to stage a smash-and-grab victory.
Jurgen Klopp's side appeared to be heading to the quarter-finals early in extra-time as they led 2-0 but an inexplicable mistake by Adrian, Liverpool's No2, changed the game and allowed Atletico substitute Marcos Llorente to score a crucial away goal.
Adrian, who was playing because of a hip injury to first choice keeper Alisson Becker, made a hash of clearing a simple pass then got himself into the wrong position as Llorente rolled the ball past him.