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Holders Spain lost for the first time in 15 matches at the European Championship finals when Croatia beat them 2-1 to win Group D at Euro 2016.
Ivan Perisic scored the winner with three minutes left on Tuesday after Croatia keeper Danijel Subasic had saved a penalty from Spain captain Sergio Ramos with 20 minutes remaining.
Croatia’s Nikola Kalinic had cancelled out an early goal from Spain striker Alvaro Morata in the first half.
Spain meet Group E winners Italy in a heavyweight last-16 tie on Monday in Paris – a rematch of the 2012 final – while Croatia will play one of the third-placed teams in Lens on Saturday.
Last night at the Euros
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» Croatia vs Spain
» Ukraine vs Poland
» Northern Ireland vs Germany
“Now we will face a more difficult rival than had we finished first in our group,” Ramos said.
Spain’s path suddenly looks more perilous.
Not only do Italy stand in the champions’ way in the round of 16, world champions Germany are then potential quarter-final opponents while hosts France and England also lie in wait as possible semi-final opposition.
“We are disappointed,” conceded Spain coach Vicente del Bosque.
“The path now might be seen as more difficult, but you never know where the danger is.”
Kalinic’s goal just before the break was the first goal conceded by Spain in 948 minutes of European Championship matches since October 2014.
Croatia’s excellence and commitment in battling back from behind condemned a jaded Spain, going for a third-straight title, to their first defeat in a European Championship finals since they were beaten 1-0 by Portugal in the 2004 group stages.
“When you play against the world’s best, you have to play like this,” Ivan Rakitic said.
“We deserve it. We gave everything until the last minute.”
Croatia overcame the disappointment of their second group match against the Czech Republic by starting confidently, seeking to set the tone with an intense press.
However, it was the Spanish who struck decisively in the seventh minute.
David Silva drove inside before sending a reverse pass out to Cesc Fabregas, whose diagonal run across the box went unnoticed by everyone else.
His cross was met by Morata, arriving at the back post, and on the day that his move back to Real Madrid from Juventus was announced, the striker touched home for his third of the tournament.
Croatia began the second half confidently and David De Gea was called into action to tip away Darijo Srna’s cross before closing down Tin Jedvaj’s follow up.
Late goals have been a theme of this tournament, and while Spain struck late to down the Czech Republic in their opener, here they were on the receiving end.
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