Germany fell to their fifth defeat in nine games after they were comfortably beaten 3-0 by the Netherlands at the Johan Cruijff Arena in Amsterdam.
After a quiet but even start to the game, it was the hosts who took the lead on the half-hour mark.
An inviting corner from Memphis Depay found Ryan Babel who saw his header crash off the underside of the crossbar, but Virgil van Dijk was there to head into an empty net from two yards out to give the Dutch the lead in front of their home fans.
A couple of inspired second half substitutes from Joachim Low looked to swing the match in Germany's favour as the visitors pushed for an equaliser.
However, the game was put to bed after Depay neatly slotted the ball past Manuel Neuer with three minutes remaining before Georginio Wijnaldum rounded off the scoring in stoppage time to secure a memorable win over their bitter rivals.
Here is a breakdown of the evening's events:
Key Talking Point
They were the better team in the 90 minutes and never looked out of place going up against a strong Germany side.
Dutch football has been in a rebuilding phase for quite sometime now, but they finally look to be producing some fine young talent and are piecing together a strong squad ready to compete with the world's elite teams.
Staring XI: Depay (9)
STAR MAN - Depay really was on top form on the night. He played as the lone striker but often found himself drifting out onto the wings and back into midfield to find the ball and run at defenders.
Memphis Depay has been electric in this game— Luke Ginnell (@HeavyFirstTouch) October 13, 2018
Feel like Real Madrid should consider going for Memphis Depay.— Daniel (@Daniel2x_1) October 13, 2018
Memphis Depay is a completely different player now.— Count Zugu (@Count_Zugu) October 13, 2018
He got his goal in the dying moments of the game with a very well-taken finish and could very easily have got a second just moments later as he saw his effort cannon off the crossbar.
Dutch fans were treated to a brilliant performance from their poster boy, who now looks to be playing full of confidence once again.
WORST PLAYER - It was a great night for Koeman and his men, however Steven Bergwijn did struggle to make an impact at times.
His performance didn't hinder his side as they still ran out 3-0 winners, however he'll certainly be hoping to contribute a lot more in their next outing and will be hoping to put his name in the headlines for the right reasons.
Key Talking Point
After drawing their opening game in the Nations League having already been dealt a tough group, Germany were in desperate search of a win to kickstart their campaign but were second best on the night.
It was their third consecutive defeat in competitive internationals and after a disappointing World Cup exit at the group stages it looks to be a very rough patch for German football.
They find themselves bottom of League A Group 1 after the embarrassing defeat, and things won't get easier for them with France awaiting them in their next game.
Starting XI: Neuer (6); Ginter (6), Boateng (6), Hummels (7), Hector (7); Muller (7), Can (5), Kimmich (7), Kroos (6), Werner (7); Uth (7).
Substitutes: Sane (7), Draxler (7), Brandt (6).
STAR MAN - There weren't too many outstanding performances from Germany's point of view, however Timo Werner certainly caused the Dutch defence the most problems and created more chances than any other player in the first half.
His presence on the field began to die down during the second half when he was moved to more of a central striking role.
However, in what was an evening to forget for many of Joachim Low's men, Werner can hold his head up high in what was a solid performance from the RB Leipzig forward.
WORST PLAYER - He didn't necessarily have a bad game, however Emre Can never looked to stamp his authority on the game. Usually such a creative member of the midfield, he struggled to create any chances for his side and never took command of the midfield.
His disappointing evening was ended just short of the hour mark, and you could tell the instant difference in Germany's play once Julian Draxler came on to replace him.
After a memorable win for the Netherlands, they'll be looking to carry their hot form forward when they travel to face Belgium in a friendly on Tuesday.
Germany will have to regroup and get back to the drawing board when they travel to face reigning World Cup winners France in the UEFA Nations League on Tuesday night.