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Iran left it late, very late, to finally find a breakthrough against Wales but scored in the 98th and 101st minutes to claim a deserved 2-0 win and leave Gareth Bale and co. heartbroken.
Iran were dominant and had almost twice as much of the ball as Wales, even hitting the woodwork on a number of occasions as Wales rode their luck and, somehow, didn't find themselves behind until the very end.
With Wayne Hennessey having been send off in the Wales goal in the 86th minute though, Iran took advantage of Danny Ward perhaps not being ready to come on and Rouzbeh Cheshmi curled in a fine opener in the eighth minute of nine added on. Ramin Rezaeian killed it off on the counterattack with the last move of the game.
Iran dominated
As early as the 17th minute Iran had the ball in the net. Ali Gholizadeh tapped into an open net when Sardar Azmoun selflessly squared to him in the six-yard box. But it was ruled out after VAR ruled it offside.
Unfortunate not to have led already, they were beyond unlucky in the 52nd minute when they hit the post twice. Azmoun was first to thump off the post after coming in from the right. The ball fell then to Gholizadeh and he crashed off the opposite upright.
Welsh heartache as Iran break through
Hennessey saw red only after VAR intervened and upgraded his initial yellow card, but he came out and cleared Mehdi Taremi out with a wild swing of his boot. He became just the third goalkeeper to ever be sent off at a World Cup. That gave Iran hope that a winner would be found.
It came as Cheshmi curled in a gorgeous low effort from the edge of the box and Iran had their historic win, seeing Welsh players fall to the ground in desperation. Rezaeian's second was just the icing on the cake.