Wales goalkeeper Wayne Hennessey was awarded the first red card of the 2022 World Cup 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.
Wales must now beat England in their final group game to have any chance of reaching the knockout stages and hope that the result between USA and Iran goes there way.
An emotional Gareth Bale said afterwards: ‘Gutting, no other way to say it, we fought until the last second. It’s one of those things that is difficult to take but we have to recover and go again.
‘We have to pick ourselves up straight away. It’s going to be difficult but we have one game left and we have to be positive and try enjoy the occasion.
‘It is going to be difficult for sure, it depends on the other game so we will see.
On Hennessey’s red card, he added: ‘I haven’t seen it so I don’t really know but obviously the red card changes the game completely.’
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