Russia have eliminated 2010 World Cup winners Spain in the tournaments first penalty shootout to secure a spot in the last eight of the competition.
Fernando Hierros side started positively at Luzhniki Stadium and broke the deadlock as Sergei Ignashevich directed the ball into his own net from a free-kick.
Sergio Ramos claimed the goal but replays showed that Ignashevich got the final touch with his heel as he battled the Real Madrid defender inside the box.
Spain enjoyed the majority of the possession as half-time approached but were unable to penetrate Russias well-organised defence and were punished in the 41st minute.
A Russian header from corner struck Gerard Piques outstretched arm inside the penalty area and Artem Dzyuba scored with the resulting spot-kick.
The hosts kept Spain at bay as the clash neared the end of normal time but substitute Andres Iniesta came close to scoring with a speculative shot from close-range.
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However, Iniestas effort was parried away by Igor Akinfeev and extra time was called in Moscow.
The first half of extra time was dominated by Spain again, with Isco at the forefront of the attacks but still unable to generate any clear cut opportunities. The best chance was Asensios long-range strike which fell right into Igor Akinfeevs hands.
Valencias Rodrigo added some much-needed energy to the wilting Spanish attack during the final 15 minutes, but again Hierros side were unable to find a way through as the Russians sat deep and defended until the eventual penalty shootout was called by the referee.
Andres Iniesta put the hosts ahead 1-0 from the spot, but Fyodor Smolov returned fire for Russia despite a hand from David De Gea in goal.
Pique was next up for the 2010 winners, and he buried his with ease into the bottom left corner. Sergei Ignashevich scored his moments later, and the score remained 2-2.
However, Koke s penalty was saved by Akinfeev before Aleksandr Golovin fired the hosts ahead 3-2.
The responsibility then fell on Ramos shoulders and he delivered, rifling his penalty in the net.
But it didnt matter, Denis Cheryshev scored Russias fourth before Iago Aspas spotkick was again saved by Akinfeev, sending Spain packing.
Russia will now face either Croatia or Denmark in the quarter-final, the first time they have reached the last eight since 1970.