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Wales lost their second group game 2-0 to Iran, leaving them with little hope of qualifying for the knockout stages of the World Cup.
They will now have to beat England to have any chance of qualifying and that may also not be enough if England and Iran can both find results against the US.
Wales’ goalkeeper Wayne Hennessey’s rash challenge late on in the match saw him sent off with the score at 0-0.
Then in the final minute of injury time Ali Karimi struck low and hard from outside the box to find the bottom corner.
And there was just enough time for Iran to add a second as Wales chased a goal, with Ramin Rezaeian lifting the ball over Danny Ward to secure all three points.
Wales started better against Iran than they did against USA with Kieffer Moore, starting ahead of Dan James, winning balls high up the pitch. An early knock-on led to a Neco Williams shot from range which flew over the bar.
But what was also evident was that Iran were going to be much tougher to beat than they were against England.
With Mehdi Taremi and Sardar Azmoun up front, Iran posed a real goal threat and created problems early on inside the Welsh box.
However, the first big chance fell to the Dragons, as Connor Roberts crossed in from the right and Kieffer Moore stretched to make contact on the volley blasting his shot straight at Hossein Hosseini who parried well.
And Wales almost immediately paid for that missed chance as Iran latched onto a loose ball from Roberts inside his own half. Azmoun broke forward and combined brilliantly with Ali Gholizadeh to work the ball towards goal, with Gholizadeh poking it home from a few yards out.
But VAR came to Wales rescue, identifying a marginal offside as the final ball was played from Azmoun - who perhaps should've taken on the shot himself.
The disallowed goal gave Iran added impetus and Azmoun went close with a header from a set-piece.
The Bayer Leverkusen striker was proving a problem for Wales, so they would've been pleased to see him go down injured with an apparent leg injury after 25 minutes.
It wasn't bad enough to force him off though and he continued to battle hard for Iran up front.
With the first-half coming to a close, Wales looked the most likely to nick a goal with some concerted pressure and balls into the box.
And with the Red Wall behind them Wales pushed to create an oppening, but Iran continued to look dangerous on the counter.
Possession: Wales 62% - 38% Iran
Shots: Wales 10 - 21 Iran
Shots on target: Wales 3 - 6 Iran
Corners: Wales 2 - 7 Iran
Red cards: Wales 1 - 0 Iran
In first-half injury time a ball swung in from the right almost found Azmoun, who couldn't quite make strong enough contact with an outstretched foot. Then Ahmad Noorollahi tried his luck from outside the box, but his shot was easily saved by Hennessey.
At the end of the half Joe Rodon received a yellow card for a rash challenge on Mehdi Taremi - perhaps pay back for a number of hefty challenges from the Iranians on the likes of Gareth Bale and Neco Williams, as well as a sneaky little stomp from Morteza Pouraliganji on Chris Mepham's foot earlier in the half.
Iran should've taken the lead early in the second half, with Azmoun striking the post after latching on to a through ball. Then seconds later Hossein Kanani curled a shot against the post from outside the box. Azmoun followed up with a header, but the rebound was blocked by Hennessey to keep the scoreline at 0-0.
Ten minutes into the second half Wales made their first subs, bringing on Brennan Johnson and Dan James for Connor Roberts and Harry Wilson.
For Iran, Azmoun finally succumbed to his calf injury with just under 25 minutes left, leaving the pitch having been Iran's biggest threat.
Iran still looked dangerous though and with 18 minutes left Joe Rodon dribbled out of defence and misplaced a pass, allowing Iran to bear down on Wales' goal. Saeid Ezatolahi took the shot on, but Hennessey did well to get down and tip the ball around the post.
Then with ten minutes to play, both sides desperately went for the win knowing that a draw would leave them with a mountain to climb in their final group fixture.
Kieffer Moore laid a ball off to Ben Davies on the edge of the box, but the Spurs defender's shot was tipped over the bar.
Then Iran played a long ball, which Hennessey raced out of his box to intercept, clashing into Taremi as he chased down the ball - there were shades of German goalkeeper Toni Schumacher's infamous challenge in 1982 against France as Hennessey's kick flew into the chest of the Iran striker.
Bizarrely the referee was only going to brandish a yellow card, but VAR intervened and the Welsh keeper was given a red - the first of the tournament.
The Iranian onslaught ensued. And in the final minute of injury time Rouzbeh Cheshmi struck low and hard from outside the box to find the bottom corner.
And the game was completely finished after 100 minutes when Iran broke away and made it 2-0, as Ramin Rezaeian lifted it over Wales stand-in keeper Danny Ward.
Wales still have a chance to qualify, but it's a slim chance.