North Macedonia produced one of the biggest shock results in qualifying so far, with a 2-1 win in Duisburg after goals from Goran Pandev and Elif Elmas.
Pandev, who has spent 15 years playing Italy’s top flight along with a brief stint with Galatasaray, opened the scoring in the 45th minute.
Germany levelled from an Ilkay Gundogan penalty before Timo Werner missed a gilt-edged opportunity to put the hosts ahead with 10 minutes to play.
Then Elmas popped up for a stunning 85th minute winner to initiate scenes of joy, along with recriminations for Joachim Low’s side.
“We’re thoroughly disappointed,” Low said. “We simply looked too tired today. There wasn’t an energy about our play and we made too many mistakes going forward.
“When we moved the ball around quickly, we looked dangerous. Our opponents sat deep and we couldn’t find a way to break them down. All in all, it was disappointing.”
Low lamented Werner’s shocking miss too. He said: “He must put that ball away, no question at all. He has shown here he can score goals.
“But he doesn’t hit the ball right with his left foot, if he makes a clean contact with the ball its a goal.”
Elsewhere on Wednesday, John Stones committed an awful defensive error allowing Poland’s equaliser before providing the assist for Harry Maguire’s winner in England’s 2-1 victory.
Antoine Griezmann’s strike was enough for France to win 1-0 in Bosnia-Herzegovina, while Spain rebounded with a 3-1 home win over Kosovo.
Greece were held to a 1-1 draw by Georgia, Italy cruised 2-0 in Lithuania and Denmark thrashed Austria 4-0 in Vienna.