North Macedonian forward Eljif Elmas scored the winner as the underdog from the Balkans ended a 20-year unbeaten run for Germany in the World Cup qualifiers in a 2-1 away win.
"The disappointment is huge," said a crest-fallen Joachim Low after the final whistle in Duisburg on Wednesday.
"This is a set-back. There were a lot of mistakes and we didn't find a way to break down the deep-standing North Macedonians. We also let them counter-attack and had no grip on the game," Low, who led Germany to the 2014 World Cup title, was quoted as saying by the Agence France-Presse (AFP).
In Group J, Germany has slumped to third place after three games – behind North Macedonia and 99th-ranked Armenia, which beat Romania 3-2 for a third straight win having trailed after 87 minutes in Yerevan.
Napoli midfielder Eljif Elmas scored the winner five minutes from time after Ilkay Gündoğan's penalty had drawn Germany level following 37-year-old striker Goran Pandev's first-half opener.
The German press were quick to put the boot in. "How embarrassing!" fumed daily Bild on their website. "Nasty Surprise" said football magazine Kicker while Frankfurt-based daily FAZ opted for "Rude awakening for the German team."
The four-time world champion has never failed to qualify for football's biggest tournament, but did not enter the inaugural edition in 1930 and was banned in 1950. However, Low's men are already languishing third in the Group J table, three points adrift of leaders Armenia and behind North Macedonia on goal difference. the Euros could cause the Germans more pain given they are in the same group as reigning champion Portugal and world champion France.
"The fact is, that shouldn't have been allowed to happen," admitted stand-in captain Gündoğan after Germany's first World Cup qualifying loss since the infamous 5-1 thrashing by England in 2001.
"It felt as though North Macedonia only got near our goal twice and scored twice, it was too easy. We had chances and only scored one goal."
"It hurts all the more that not much will happen for two months," he added as Germany does not play again until its Euro 2020 warm-up matches in June. "We have to get in top shape by the end of May and prepare for the (European championship) tournament."
Germany faces world champion France and European title-holder Portugal in its Euro 2020 qualifying group. The defeat was just the latest setback suffered by Germany, after their 6-0 drubbing by Spain last November in its worst defeat since 1931, and the shock group-stage exit at the 2018 World Cup in Russia.
The loss, which ended an 18-match winning streak in World Cup qualifying, will put pressure on Low, who will step down following the Euro 2020 finals in July after 15 years in charge.
The result will also weigh on struggling Chelsea striker Timo Werner, who squandered a golden chance with the score 1-1 after coming off the bench in the second half. The former RB Leipzig striker has now scored only two goals in his last 31 appearances for club and country.
"I'm sorry for him (Werner)," admitted Gündoğan.
North Macedonia is ranked 65th in the world, 52 places below Germany, but it was the visitors who took the lead in Duisburg. Germany was made to pay for missing several early chances, including a skied shot by Bayern Munich winger Serge Gnabry with the goal at his mercy.
In added time at the end of the first half, North Macedonia's Pandev fired home his 38th international goal.
Germany was suddenly faced with failing to win a World Cup qualifier for the first time since being held to a 4-4 draw at home by Sweden in 2012.
With an hour gone Gündoğan, Germany's captain for the night with Manuel Neuer rested, stepped up to convert the resulting penalty after Leroy Sane went down in the area.
After Werner's howler, North Macedonia took its chance when Dinamo Zagreb's Arijan Ademi beat Werner's Chelsea teammate Antonio Rudiger and squared for Elmas to fire past Germany goalkeeper Marc-Andre ter Stegen.
Before kick-off, the Germans revealed a banner with the words "Wir sind 30" (We are 30), in black-red-gold lettering, referring to the United Nations' 30-point declaration of Human Rights.
It was the third straight match where the Germans have made a protest aimed at 2022 World Cup hosts Qatar. Several other nations including Denmark, Belgium, the Netherlands and Norway have also protested for human rights before their qualifiers over the last week.
Qatar has faced criticism for its treatment of migrant workers, many of whom are involved in preparations for next year's tournament, while Qatari authorities insist they have done more than any country in the region to improve worker welfare.
