Germany suffered a first World Cup qualifying defeat since being thrashed 5-1 by England 20 years ago following a shock 2-1 home loss to North Macedonia.
Eljif Elmas struck five minutes from time to secure a major upset in Duisburg and move the visitors level on six points with Joachim Low's side in Group J.
The four-time world champions had been unbeaten in 31 successive World Cup qualifiers – dating back to the visit of Sven Goran Eriksson's England to Munich in September 2001 – and looked to have salvaged a point after Ilkay Gundogan's penalty cancelled out Goran Pandev's opener.
Armenia are the surprise early front runners in that group after maintaining their 100 per cent start by mounting a late comeback to stun 10-man Romania with a 3-2 win.
A second-half double from Alexandru Cicaldau overturned Eduard Spertsyan's debut goal to give the visitors the lead in Yerevan but, after George Puscas was dismissed for a dangerous challenge on Andre Calisir, Varazdat Haroyan levelled four minutes from time before Tigran Barseghyan won it with an 89th-minute penalty.
