Wales goalkeeper, Wayne Hennessey, on Friday became the first player to be shown a red card at the 2022 World Cup.
Hennessey was sent off for a horror challenge on Iran forward Mehdi Taremi.
The 35-year-old had, minutes, earlier made one of the saves of the tournament when he dived low to his left to deny Saeid Ezatolahi but turned villain soon afterwards following a rush of blood to the head.
Hennessey sprinted out of his goal in an attempt to deny Taremi but succeeded only in flattening the Iran striker with a flying knee.
The Nottingham Forest back-up keeper appeared to have earned a reprieve when referee Mario Escobar initially awarded him a yellow card before he was encouraged to visit the pitchside monitor and quickly reversed his decision.
Iran had been the better team throughout the contest and had a first-half goal from Ali Gholizadeh correctly ruled out for offside by VAR.
Carlos Quiroz’s side, who were booed ahead of kick-off while they sung their national anthem, came even closer with 20 minutes remaining when they hit the post twice within the space of a few seconds.
Iran, however, made their numerical advantage tell in the closing stages when Roozbeh Cheshmi’s raking shot beat Hennessey’s replacement, Danny Ward, from distance eight minutes into stoppage time, before Ramin Rezaeian made the victory safe 60 seconds later.
