Wales goalkeeper Wayne Hennessey was sent off for a kung-fu kick

But there was nothing they could do to stop Rouzbeh Cheshmi from scoring a great goal to put Iran ahead in stoppage time. The 29-year-old picked the ball up on the edge of the box and let it fly from range with his effort flying past Ward into the bottom right corner.

Wales players fell to the ground simultaneously as Cheshmi was hounded by his teammates to spark wild celebrations. Page’s side then threw everything he had to find a late equaliser, but were left exposed at half-time.

Iran responded quickly in the dying seconds of the match with Ramin Rezaeian contributing Iran’s second of the game to compound Wales’ misery. Wales are now bottom of Group B and need a win against England on Tuesday to have a chance of qualifying for the round of 16.

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