Holland were left on the verge of exiting Euro 2012 at the group stage on Wednesday just two years after they looked set for a golden era when they reached the World Cup final.
Two goals by German striker Mario Gomez proved enough as the Euro 2008 finalists saw off the Dutch 2-1 and left them pointless after two games of Group B.
The Dutch will have to beat Portugal in their final group game.
That looks an even tougher task after a stunning strike by substitute Silvestre Varela three minutes from time gave them a 3-2 win over a resilient Danish side that had come back from 2-0 thanks to two Nicklas Bendtner headers.
Germany lead the group on six points while the Danes and the Portuguese have three apiece.
Gomez struck twice in the first-half, both goals created by Bastien Schweinsteiger, to take his tally to three for the tournament and level with Russia's Alan Dzagoev at the top of the scoring charts.
Whilst Robin van Persie got one back in the second-half, some relief for coach Bert van Marwijk whose loyalty to the Arsenal star had started to look foolhardy in the extreme after a woeful first-half, the Dutch still came up short.
More worrying still ahead of a must win game was Arjen Robben's show of petulance when he was replaced late on.
He showed his disgust by walking off the opposite side of the pitch and sullenly walked round to the side of the dugout.
Added to the discontent publicly expressed by Klaas-Jan Huntelaar and Rafael van der Vaart it does not augur well for the lead-up to the Portugal clash, though, the coach tried to drum up some enthusiasm for the challenge.
"We still have a chance to go through and we have to believe in it," said van Marwijk defiantly.
"Thousands of fans have come here and we have to do well for them, we have to beat Portugal now to have a chance."
For his German counterpart Joachim Loew the 'door was now open to the quarter-finals' and he did not exactly give a ringing endorsement of Holland's chances of getting the win they need at the very least.
"Holland created a few chances, which our defence dealt with, but I had the feeling Holland were physically dead after 60 minutes."
Portugal made life more difficult for themselves than they should have done and would have been easy winners had not their start player and captain Cristiano Ronaldo not missed a hatful of chances.
The Real Madrid hotshot was also ridiculed after the last of his misses by hearing the Danish fans chant the name of his Argentinian nemesis in the Spanish league scoring charts Lionel Messi.
But he had a pithy riposte.
"Do you know what he (Messi) was doing this time last year? He was going out of the Copa America in the quarter-finals."
Ronaldo will hope that his campaign lasts even that far.
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