Netherlands failed to book a place in the play-off stage of Euro 2016 qualifying following a 3-2 defeat at home to 10-man Czech Republic.
Danny Blind’s side needed to win their final Group A fixture and hope Iceland beat Turkey in order to finish in third place, but were unable to do their part and Fatih Terim’s men won in Konya anyway.
After a positive start from the hosts, Pavel Kaderabek and Josef Sural fired Czech Republic into a two-goal lead inside 35 minutes, drawing jeers from the Amsterdam Arena crowd.
Home spirits were lifted when Marek Suchy was dismissed for his challenge on Memphis Depay on the stroke of half-time.
However, Robin van Persie – making his 101st Netherlands appearance as a first-half substitute – put through his own net in the 66th minute.
Klaas-Jan Huntelaar pulled one back four minutes later and Van Persie scored his 50th international goal in the 83rd minute, but a win would not have been enough anyway given Turkey’s victory as, fittingly, Blind’s team ended a dismal qualification campaign in defeat.
Netherlands wasted no time in setting about their task, with Anwar El Ghazi calling Petr Cech into action inside the opening minute before Wesley Sneijder blazed over nine minutes later.
But Netherlands’ desire to push for an opener left them exposed defensively, and Czech Republic soon began to capitalise on that.
Jeroen Zoet needed to be bailed out by Virgil van Dijk after spilling a Sural cross at the feet of Theodor Gebre Selassie, and in the 24th minute the visitors broke the deadlock.
A slick move through the centre of the pitch was completed by Kaderabek, who guided the ball beyond Zoet at his near post following a pass from Jiri Skalak.
Whistles rang out inside the Amsterdam Arena as the Dutch adopted a more conservative approach, but 11 minutes later the deficit increased.
Tomas Necid found Sural in the box and he lifted the ball over a weak challenge from Van Dijk before sliding a finish into the back of the net.
With his team in dire straits, Blind replaced Jairo Riedewald with Van Persie.
And Dutch hopes of turning the game around were given a boost two minutes before the interval as last man Suchy was shown a red card for bringing down Depay.
Van Persie and Depay both passed up opportunities to test Cech early in the second half so Blind made another attacking change – Bas Dost on for Van Dijk.
Netherlands’ lack of ingenuity proved costly in the 66th minute as Van Persie headed a Skalak free-kick into his own goal to compound the hosts’ misery.
Huntelaar restored a modicum of respect four minutes later as he climbed above Vaclav Prochazka to nod Sneijder’s corner past Cech.
Van Persie then reduced the deficit to a single goal, stabbing a flick-on from Dost beyond Cech with seven minutes remaining.
The damage had already been done, however, with Netherlands finishing fourth in the group while Czech Republic leaped above Iceland to take first place.