Two late goals by Iran have left Wales’ World Cup hopes hanging by a thread.
Goals scored by Rouzbeh Cheshmi and Ramin Rezaeian in stoppage time gave Wales their first loss of the campaign.
It came after Wales goalkeeper Wayne Hennessey was shown a red card late in the match.
He came steaming out of his penalty area and missed an attempted clearance, clattering Iranian striker Mehdi Taremi in the process.
Initially given a yellow card, following a VAR check after protests from the Iranian team, match referee Mario Escobar changed his mind and sent the Welsh goalie off the pitch, reducing the Welsh side down to 10 men.
Rob Page’s team were rattled at times during the match, with Iran continuously issuing reminders of the danger they posed.
Iran hit the post twice and then goalkeeper Wayne Hennessey – within seconds – during one explosive counter attack in the second half.
Wales rarely tested the Iranian defence, and appeared to be relying on another moment of magic from captain Gareth Bale.
The introduction of Daniel James and Brennan Johnson gave Wales more attacking potency, but Iran still looked a threat at the other end.