Cristiano Ronaldo buried a 68th-minute penalty to end a two-decade wait for a World Cup knockout goal, sparking Portugal’s 2-1 comeback victory over Croatia in the Round of 32 at Toronto’s BMO Field. After Ivan Perišić had headed Croatia in front in the 53rd minute, Ronaldo saw a close-range finish ruled out for offside before VAR intervened for a foul by Nikola Vlašić on Renato Veiga away from the ball. The 41-year-old sent the goalkeeper the wrong way from the spot, levelling the match and igniting the Portuguese bench.

The strike was Ronaldo’s 11th in World Cups, making him the oldest goalscorer in knockout-stage history at 41 years and 147 days, surpassing the mark held by former teammate Pepe. It also ended a drought that had stretched across eight previous knockout appearances since 2006, and made him the first player to score in six different editions of the tournament. Opposite him, Croatia captain Luka Modrić started at 40 years and 296 days, making it the first men’s World Cup knockout match to feature two outfield players over 40.

Ronaldo was replaced by Rúben Neves in the 81st minute, visibly frustrated by the decision, but the substitution paid off deep into a chaotic second half that produced 19 minutes of added time. Substitute Gonçalo Ramos rose to head in Rafael Leão’s cross in the 90+4th minute, and Croatia’s last-gasp equaliser from Joško Gvardiol in the 90+13th minute was disallowed for offside after a frame-by-frame VAR review, prompting Croatian fans to throw objects onto the pitch.

Portugal advance to face Spain in an Iberian Round of 16 clash on Tuesday, while Croatia exit a tournament that may prove to be the final World Cup appearances for Modrić and Perišić.