The Netherlands’ hopes of qualifying automatically for Euro 2016 were ended by a heavy defeat in Turkey.
Midfielder Oguzhan Ozyakup raced on to an Arda Turan through ball to put the home side ahead with a chipped finish.
Turan doubled the lead by stealing the ball from a dithering Daley Blind before firing past the weak hands of Jasper Cillessen at the near post.
Burak Yilmaz added a third late on to seal a result that means the Dutch can only finish third in Group A.
But to achieve that the Netherlands must now rely on Turkey dropping points in their last two games.
Iceland confirmed their place at an international tournament for the first time when they secured the point they needed against Kazakhstan. The Czech Republic also qualified automatically after beating Latvia 2-1.
Whoever finishes behind the top two will be guaranteed a place in a two-legged play-off against another of the third-placed sides.
That is the only path open to the Dutch, but their fate is now out of their own hands after Turkey leapfrogged them with a convincing win.
It was the Netherlands’ heaviest competitive defeat since 1996, when they lost 4-1 to England at Wembley in Euro ’96.
“This whole qualification campaign has been incredibly difficult,” said striker Robin van Persie. “We still have a chance, but it is no longer in our hands and that is terrible.”
What next for Netherlands?
Netherlands play Kazakhstan away on 10 October before their final group match at home to Czech Republic three days later, while Turkey may have a more difficult run-in, playing Czech Republic away and Iceland at home.
The last time the Dutch failed to qualify for a major tournament was the 2002 World Cup. Before that, they were absent from the 1982 and 1986 stagings and from the 1984 European Championship.
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