Goncalo Ramos scored a dramatic stoppage-time header to give Portugal a 2-1 victory over Croatia and a place in the World Cup last 16, where they will face Spain.
The decisive moment came in the fourth minute of added time in Toronto. The win was confirmed after a last-gasp Croatian equalizer was ruled out for offside following a VAR review.
Croatia had taken the lead through Ivan Perisic in the 53rd minute. Portugal's captain, Cristiano Ronaldo, then made history. The 41-year-old converted a penalty in the 68th minute, becoming the oldest player to score in a World Cup knockout stage and netting his first-ever goal in that round of the tournament.
Portugal dominated possession early but struggled to break down a resilient Croatian side. The game remained tense until Ramos's late intervention secured the win.