Croatia knocked out dogged Denmark in a shootout to set up a World Cup quarter-final tie against hosts Russia while Danijel Subasic saved three penalties.
It came at the end of a largely disappointing tie - and one that had seen Luka Modric spurn a golden chance to snatch a late winner when his penalty shortly before the end of extra-time was superbly saved by Kasper Schmeichel.
Two penalties were saved by the Leicester City goalkeeper in the shootout at the Nizhny Novgorod Stadium but he could not prevent Ivan Rakitic slotting home the decisive 10th kick.
The match ended on a super dramatic note and started that way as well.
Martin Jorgensen capitalised on the chaos caused by a long throw to fire a weak shot beyond Subasic in the opening minute.
The second half of the match was particularly dreadful and seemed to have an inevitability of penalties from well before the start of extra-time.
Croatia were wonderful the last time they played in Nizhny Novgorod, lowering Argentina 3-0 and setting out a genuine marker than they are contenders here in Russia. But they were a shadow of that side on Sunday.
Back in Euro 2016 Croatia passed up a major opportunity for winnable ties against Poland and Wales - and they would prefer not to do leave behind an opportunity to dive deep once more.
Denmark had just once already achieved the last eight of the World Cup - losing to Brazil at France 98 - however Age Hareide's side can see themselves as tragic to have lost against Croatia.
They started the game with their first-minute objective, which saw Huddersfield's Jorgensen shoot between the legs of two Croat protectors and annihilation Subasic with what was an exceptionally saveable shot.
Denmark made a colossal commitment to the most exceedingly bad round of the competition so far when they and France played out a commonly advantageous, flat goalless attract their last gathering match.
However, they can't be blamed for ruining this tie in Nizhny Novogorod, in spite of the fact that in truth they presumably leave the World Cup at a phase that is proportionate with their capacity.
Kasper Schmeichel was declared as the Man of The Match
Croatia coach Zlatko Dalic stated, "It was a very difficult game. We conceded in the first minute, then we equalised. We missed a sitter. We miss penalties. We had chances but we stayed strong, mentally composed, and we won eventually."
Denmark goalkeeper Kasper Schmeichel stated, "It's a strange feeling. Huge disappointment. But also enormous pride about our team.”
He further added, “I think today we had the opportunity. I think we were the better team in the second half and the extra-time. I don't think we had any luck. I don't think the referee liked us today. It is difficult to accept and put into words. There are many emotions right now."