Portugal’s World Cup dream ended in heartbreak on Monday night as Spain edged them 1-0 in a tense round-of-16 clash at AT&T Stadium in Arlington, Texas, in what is widely believed to be Cristiano Ronaldo’s final World Cup appearance.

Substitute Mikel Merino settled a tightly contested and largely uneventful affair with a stoppage-time strike in the 91st minute, breaking Portuguese hearts and sending Spain through to the quarterfinals, where they will face the winner of the USA-Belgium tie.

The match had been billed as one of the standout fixtures of the knockout stage, pitting Iberian rivals against each other with a place in the last eight on the line. Neither side managed to fully live up to the occasion for long stretches, though both had glimpses of quality.

Spain’s Mikel Oyarzabal squandered a golden opportunity early on when he raced through one-on-one but fired wide, while Portugal’s best chance came from Nuno Mendes, whose deflected effort cannoned off the crossbar after beating Spanish goalkeeper Unai Simón. The game remained goalless deep into the second half until head coach Luis de la Fuente’s substitutions changed the complexion of the match. Ferran Torres, introduced from the bench, slipped a delicate pass into the box, and Merino arrived unmarked to finish coolly past Diogo Costa, sparking wild celebrations among the Spanish contingent. Portugal nearly salvaged a draw in the dying moments when Bernardo Silva rose to meet a header that beat Simón, only for the ball to sail narrowly over the crossbar.

For Ronaldo, the defeat brings the curtain down on a remarkable World Cup career spanning six tournaments and 27 appearances, the second-most in the competition’s history behind Lionel Messi. The 41-year-old finishes with 11 World Cup goals, including a brace against Uzbekistan and a penalty against Croatia in this year’s edition, and he remains the only player to have scored at six different World Cups.

Visibly emotional after the final whistle, Ronaldo wiped away tears and applauded the traveling Portuguese fans before speaking candidly to reporters. He said he was leaving with a clear conscience, having given his all, and that while this had indeed been his last World Cup, he would take time with his family before making any further decisions about his international future. Despite the disappointment, he pointed to the 2016 European Championship triumph as a career highlight he considers on par with a World Cup title.

The result also marks the end of Roberto Martínez’s tenure as Portugal manager, with the Spaniard stepping down following the exit. Martínez insisted the team had not failed, praising Ronaldo’s leadership and influence both on and off the pitch throughout his time in charge. Portugal will now have to wait until the next World Cup, co-hosted by Portugal, Spain, and Morocco in 2030, for another shot at the trophy that has eluded Ronaldo throughout his storied career, by which time he would be 45 years old. Spain, meanwhile, continue their campaign with growing confidence as they look ahead to a quarterfinal showdown against either the United States or Belgium.

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