Cristiano Ronaldo missed a stoppage-time penalty and his Saudi Pro League club Al Nassr were eliminated from the King's Cup in a 1-0 loss to Al Taawoun.
The five-time Ballon D'Or winner has yet to win a major trophy since signing for the club almost two years ago.
Playing at the round-of-16 stage of Saudi Arabia's premier knockout competition on Tuesday, Al Taawoun took the lead on Waleed Al-Ahmad's header with 20 minutes remaining. Al-Ahmad was then whistled for a foul in the area in the 95th minute.
Ronaldo had converted all 18 of his previous penalties for Al Nassr but this time shot over the bar and drew shock from the home crowd of 14,519 at Al-Awwal Park in the Saudi capital Riyadh.
The ball knocked over a young fan who was filming the Portuguese icon with his phone in the stands behind the goal.
Ronaldo has scored 73 goals in his 82 appearances for Al Nassr since joining the club in December 2022.
The defeat is the first for Stefano Pioli since the Italian succeeded Luis Castro as head coach in September.
Ronaldo and Al Nassr still have two chances at silverware this season but are already six points behind leader Al Hilal after eight games in the league, and have seven points from three games in the group stage of the Asian Champions League.
“Technically we performed well but we couldn't win the game,” Pioli said.
“We feel disappointed to be out of the cup. But we still have two trophies to go for and we will give our best in them.”
