North Macedonia stunned four-time world champions Germany as Eljif Elmas' late goal secured a shock win.
Goran Pandev had put North Macedonia ahead in the 2022 World Cup qualifier on the stroke of half-time.
Ilkay Gundogan equalised from the penalty spot early in the second half after Leroy Sane had been fouled.
But North Macedonia, ranked 65th in the world, snatched victory with five minutes remaining when Elmas struck from close range.
Chelsea forward Timo Werner missed a glorious chance to score for Joachim Low's side before North Macedonia's winner but somehow fired wide from close range.
'We've never beaten a team with so many titles'
It was a first defeat in Group J for Germany and the first goals they had conceded in qualifying.
The loss also ended their 35-game unbeaten run in World Cup qualifying, stretching back to theirĀ 5-1 defeat by England in 2001.
"This is bitterly disappointing," Low said.
"We were not fresh enough, we made mistakes. When we played quickly we were dangerous but we did not find the tools to be really threatening.
"Overall, it was disappointing to lose like that at home."
North Macedonia's win was their second in Group J and means they are second with six points, three behind leaders Armenia with Germany third.
"These lads have made North Macedonia proud against the winners of four World Cup titles and three European championships," North Macedonia coach Igor Angelovski said.
"We've never beaten a team with so many titles. Now we have to get some rest as what we have accomplished still hasn't sunk in."
Before kick-off, Germany's players unfurled a banner supporting human rights.
Germany players also wore T-shirts to show support for Qatar migrant workers before their World Cup qualifying win over Iceland on Thursday.
Latest Stories
-
Stonebwoy, other African acts’ music restored after TikTok, Universal Music resolve dispute
13 mins -
Dumsor hasn’t ended – IES debunks Akufo-Addo’s claim as citizens complain of more outages
20 mins -
‘Man stuffing ballot box, not our staff and incident not related to Ejisu by-election’ – EC
35 mins -
Agogo Presby Hospital holds annual performance review meeting
40 mins -
Fifth body found after Baltimore bridge collapse
50 mins -
Atlantic Lithium to list on the Ghana Stock Exchange
54 mins -
EOCO could have done more investigations into Cecilia Dapaah’s case – GII
1 hour -
MTN FA Cup: Dreams FC to switch focus to title defence after CAF Confederation Cup elimination
1 hour -
New photo marks Princess Charlotte ninth birthday
2 hours -
Dafeamekpor files appeal against dismissal of request to compel Akufo-Addo to accept anti-LGBTQ bill
2 hours -
Group submits RTI application seeking information on BVRs for limited registration exercise
2 hours -
They accepted my lunch offer – Kwadaso MP on money given to EC officials
2 hours -
KAIPTC launches 5-year strategic plan
2 hours -
Akwaboah Jnr stuns fans with wedding announcement
2 hours -
Chiefs not mandated to rise to greet visitors – Atuguba questions Chieftaincy Ministry justification
2 hours