A dramatic late show from Iran gave them a deserved 2-0 win over Wales, their first ever win over European opposition.
Kieffer Moore was handed a place in the starting lineup for Wales after a superb substitute performance against USA, and duly forced a save from Hossein Hosseini in the early stages of the game.
It was Iran that first had the ball in the back of the net, but Ali Gholizadeh went too early with his run and was ruled to be offside.
The game sprung into life early in the second half when Sardar Azmoun hit Wales’ right-hand post, and just seconds later hit the left-hand post with a curling effort.
As Iran ramped up the pressure Wayne Hennessey was called into action, making an excellent save low to his right-hand side on a shot from Saeed Ezatolahi.
After a good move from Wales, Ben Davies forced Hosseini to tip his powerful shot over the bar, before Wayne Hennessey was sent off after a VAR review for a crazy challenge on Mehdi Taremi outside the box.
With substitute goalkeeper Danny Ward between the sticks, Iran almost had the lead late on when Medhi Torabi’s shot went inches wide of the post.
It was heartbreak for the Welsh as – with their defence sucked deep and out of position – Rouzbeh Cheshmi fired home in the ninth minute of stoppage time.
And it was soon 2-0 as Iran broke away and Ramin Rezaeian beat Ward with a chipped goal to leave Wales in despair.