Lucas Hoeler scored a 95th-minute penalty as Freiburg came from behind to knock Bayern Munich out of the German Cup in the quarter-finals.
Bayern took the lead through Dayot Upamecano’s header but Nicolas Hoefler equalised eight minutes later.
Hoeler converted from the spot after Jamal Musiala handled in the box to book Freiburg’s semi-final place.
It was Thomas Tuchel’s second game in charge after Bayern beat Borussia Dortmund 4-2 in the league on Saturday.
The Munich club sacked boss Julian Nagelsmann after they dropped behind Dortmund in the Bundesliga table and replaced him with Tuchel, who managed their rivals from 2015 to 2017.
Tuchel’s side dominated the cup tie for large parts but Hoefler’s rocket from outside the box after Kingsley Coman scuffed a clearance drew Freiburg level and Hoeler’s late spot-kick sealed a shock win.
Freiburg lost last year’s final on penalties to RB Leipzig while Bayern have failed to reach the last four for the third successive year.
Elsewhere Randal Kolo Muani scored twice in as many minutes to secure Eintracht Frankfurt’s progress in the cup with a 2-0 win against Union Berlin.