Wayne Hennessey was sent off with a moment of madness as Wales suffered a heartbeaking 2-0 defeat to Iran on Friday to leave their World Cup last 16 hopes in tatters.
Goalkeeper Hennessey was given a red card for serious foul play with four minutes left to play and Wales were then undone by two goals in stoppage time.
Hennessey came charging out of his penalty area and took out Iran striker Mehdi Taremi around 35 yards from goal with a high boot.
The Nottingham Forest goalkeeper initially picked up a booking for the challenge, much to the outrage of the Iran team and supporters in the stadium.
However, the referee then consulted with VAR and opted to change the goalkeeper’s booking to a straight-red card.
Hennessey is only the third goalkeeper ever to receive a red card at the World Cup, after Itumeleng Khune for South Africa v Uruguay in 2010 and Gianluca Pagliuca for Italy v Norway in 1994.
With Hennessey coming off the pitch, he was replaced in goal by Danny Ward with Aaron Ramsey the outfield Wales player to be replaced with just four minutes of normal time remaining.
Wales looked to have done enough to hold out for a draw but Iran found the opener eight minutes into stoppage time.
A poor Joe Allen clearance fell to substitute Roozbeh Cheshmi, who lashed a shot from outside the box beyond Ward.
Iran then struck a second almost immediately as Rezaeian raced clear and kept his cool to clip the ball over Ward.
Wales now must England on Tuesday to stand any chance of progressing to the last 16.