The Coppa Italia descended into madness as Cristiano Ronaldo missed a penalty seconds before Ante Rebic was sent off.
Juventus had the chance to take the lead on the night and in the tie after AC Milan full-back Andrea Conti handled in the area.
Ronaldo had taken a corner down on his chest, before Conti turned into the ball and was later penalised following a VAR check.
But for the first time in his Juventus career, Ronaldo failed to covert from the spot.
Playing for the first time since the restart in Italian football, the Portuguese icon dragged his effort wide, hitting the post.
Ronaldo was left heads in hands as the tie remained at 1-1.
The 35-year-old had scored 14 consecutive penalties for the Italian champions up until that point.
His last miss from the spot came in 2019 while playing for Portugal.
The drama in the Italian cup did not stop there, though, as moments after Ronaldo’s failed penalty Milan cleared the ball down field into the path of Danilo.
But forward Rebic clattered into the Brazilian and was sent off to cap off a minute of unbelievable scenes in Turin.