Cristiano Ronaldo’s final World Cup appearance came to a heartbreaking end as Spain secured a 1-0 victory over Portugal in a tense Round of 16 match on Tuesday in New York. The decisive goal was scored in stoppage time of regular play, when Mikel Merino netted the winner for Spain.

The match remained scoreless throughout the 90 minutes until Merino’s strike in the first minute of added time. Despite Portugal’s sustained efforts and several chances to break the deadlock, they were unable to find an equalizer.

Ronaldo, participating in what has been widely reported as his last World Cup, appeared determined to lead his team deep into the tournament, but Spain’s organized defense and tactical discipline ultimately stymied Portugal’s attack.

Spain now advances to the quarterfinals, where they will face their next opponent following this victory. Portugal’s campaign ends with the elimination, marking a poignant conclusion to Ronaldo’s storied international career.