Russia were the better side throughout a match that was ordinary for the most part, with the usual Euro 2008 late drama sealed by a virtuoso performance from little Andrei Arshavin, who must now be the main candidate for player of the tournament.
And the Dutch – so impressive when they convincingly beat World Cup finalists Italy and France in the group stages – were frankly poor by their high standards.
Roman Pavlyuchenko thought he had won it for Russia when he finished from close range in the second half, but a late Ruud van Nistelrooy header forced extra-time.
Pavlyuchenko also hit the bar on 97 minutes as the Russians had several chances to win it in the additional 30 minutes, and they finally took them when Dmitry Torbinskiy and then Arshavin scored the winning goals as the clock wound down to the drama of a penalty shoot-out.
The win allowed Russia’s Dutch boss Hiddink to complete the treason he had threatened, while outgoing Oranje boss Marco van Basten was left rueing what could – and arguably should – have been for a Dutch side who performed their classic party trick of peaking too early in tournaments.
An even if uneventful first half saw the Russians impress while in possession whereas the Dutch looked dangerous from set-pieces.
Yuri Zhirkov went close with a sixth-minute free-kick that Edwin Van der Sar was forced to touch behind for a corner, from which Russia had successive chances from Denis Kolodin and Pavlyuchenko.
The Netherlands had the next two opportunities, through Orlando Engelaar’s drive wide and a Van Nistelrooy miss when Rafael van der Vaart sent a brilliant free-kick to the far post.
Van der Sar was called into action again when he made a great low save after playmaker Arshavin tricked his way into a shooting position, while the corner that followed was cleared to Kolodin, who hammered a ridiculous shot from 35 yards that Van der Sar again kept out.
Defender Kolodin was finding his shooting boots, and when the resultant set-play again dropped to him near the halfway line he cracked another incredible effort that whistled just wide.
The Dutch were on the rack, but Russia still looked vulnerable at the back. Kolodin in particular could not match his attacking prowess with defensive nous, and almost let Van Nistelrooy in before he handed a chance on a plate to Van der Vaart, who was denied by keeper Igor Akinfeev.
At the break, Van Basten brought Robin van Persie on for the ineffectual Dirk Kuyt. It started well enough for them, with Nigel de Jong unlucky not to connect with another good Van der Vaart free-kick after poor marking.
But knock-out tournament specialist Hiddink drew first blood against his homeland.
Ten minutes into the second half Arshavin played a cute pass into Sergei Semak on the left, who whipped in a superb cross to Pavlyuchenko who atoned for his early miss with a simple finish past the helpless Van der Sar.
Van Basten could see things slipping away from his team and made a bold move when he brought on John Heitinga – a threat at set pieces – and the attack-minded Ibrahim Affelay.
It was still Russia, however, who looked more likely to add to their tally.
First Pavlyuchenko found right-back Alexander Anyukov on the overlap who hammered in a shot across goal that Van der Sar saved in style.
And then Joris Mathijsen almost gifted a second to Pavluchenko when he let a high ball bounce over his head, only for Van der Sar again to deny Russia.
Netherlands huffed and puffed but Russia were holding firm, and a long-range effort from Wesley Sneijder was the closest they came to levelling.
Zhirkov could have doubled the lead as his side tried to walk the ball in, but a poor first touch meant he had to cut the ball back to Pavlyuchenko when shooting was the desired option.
But with four minutes left, Russia’s inability to defend set pieces was finally exploited. From the left wing, Real Madrid midfielder Sneijder swung a dangerous free-kick into the box to which Russia’s back four got nowhere near.
They also failed to track Van Nistelrooy, who flew in with a diving far-post header to make it 1-1.
There was a brief scare for Russia in injury-time when Kolodin was shown a second yellow for a foul on Sneijder, but the double-whammy of going down to ten men and having to defend another free-kick was cancelled by the assistant referee, who told Slovakian whistle-blower Lubos Michel that the ball had gone out of play moments before the challenge.
Arshavin – who was the co-architect of Zenit St Petersburg’s UEFA Cup triumph with another Dutch coach, Dick Advocaat – then went close five minutes into extra-time when he fired over after making space in the box.
And just afterwards, Pavlyuchenko picked the ball up on the left wing and unleashed a brilliant drive that clattered off the angle of post and bar with Van der Sar beaten.
It was all Russia. Substitute Torbinskiy finished weakly into the body of Van der Sar after yet more devilish work from Arshavin, while Kolodin sent a long-range free-kick fizzing inches wide.
They had a great shout for a penalty turned down when Zhirkov was brought down by Heitinga, and it seemed as if it was going to be a painful night for Russia when Torbinskiy then missed a sitter.
But yet more magic from Arshavin won the match. On 11 minutes he raced down the left and swung a brilliantly-improvised far post lob to Torbinskiy who – having just been booked and ruled out of the semi – somehow flicked the ball with the outside of his left boot, from an impossible angle, to beat Van der Sar and send the white-clad underdogs into raptures.
And the win was sealed when, from a quick throw, Arshavin snuck behind the Dutch defence to drill a low shot under Van der Sar with four minutes of extra-time remaining.
It was a fitting end to a quite superb display from Russia, who will face the winners of Italy and Spain’s quarter for a place in the final.
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