Wales headed into their second World Cup group stage game against Iran knowing the winners would put them in an excellent position to qualify for the last 16.
Having opened up with a 1-1 draw against the United States thanks to a late Gareth Bale penalty, the Dragons were again slow and cumbersome and failed to make many clear opportunities on goal.
Rob Page’s side were attempting to hold on for a draw but their task was made so much more difficult by a rush of blood to the head of Wayne Hennessey.
It was a major self-inflicted wound as Wales were hit on the break from a corner of their own. Mehdi Taremi looked to burst clear of the Welsh backline, but Crystal Palace stopper Wayne Hennessey came charging out of his box and missed the ball with a wild scissor kick, leaving Taremi in a heap on the floor.
Aaron Ramsey was sacrificed so Danny Ward could pick up the gloves, but Wales struggled a player down and simply could not hold off Iran before the Western Asian nation struck a late winner.
Roozbeh Cheshmi lined one up from distance to beat Ward in the 98th minute, handing Wales a major blow for their qualification hopes.
It got even worse minutes later as Ramin Semeskandi kept his cool to convert Taremi’s pass with a cool chipped finish.