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West Ham fell to defeat at Freiburg in the first leg of their Europa League last-16 tie.
The Hammers beat their Bundesliga counterparts twice in the group stage and were looking fairly comfortable until Michael Gregoritsch pounced soon after coming off the bench.
The Austrian lost several defenders to tap in Roland Sallai's mis-hit shot across the penalty area nine minutes from time.
The Hammers thought they were going to get a penalty in injury time, but after a long Video Assistant Referee (VAR) check for a potential Noah Weisshaupt handball, it was not given.
"I believe it's a penalty kick," said West Ham boss David Moyes afterwards. "In Europe they nearly give all the handballs. I don't believe it's the right way to go about it but I think that's the way Uefa work.
"I find it difficult to see why not. It was harsh on us."
His side should have been ahead long before Freiburg's goal though.
Jarrod Bowen and Lucas Paqueta both missed the target from fine Mohammed Kudus crosses, and Bowen's curling effort from the corner of the box was well saved by Noah Atubolu.
This was only Freiburg's second win in 90 minutes in any competition in 2024.
West Ham must win next Thursday in London to have a chance of following on from their last two European runs.
West Ham's players and boss Moyes were furious with the officials right at the end because they thought they should have had a penalty.
A VAR check, which lasted several minutes and included referee Alejandro Hernandez Hernandez going to the monitor, checked if Weisshaupt had handled the ball in the box.
The German had his hands in the air when Tomas Soucek, standing behind him, hooked the ball against his arms.
But the referee stuck with his initial decision of no penalty and immediately blew the final whistle.
Moyes continued: "Soucek kicks it up onto his arms. When two arms are above your head it's nearly always given because the arms are not in a natural position.
"Someone is trying to claim there was a push but then play should restart with a free-kick which he didn't do. If anything, technically the player who went to clear it probably made a mess of his clearance. That should probably be punished as well if he kicked it on to his own arm."
West Ham failed to score in a European game for the first time since a 1-0 defeat at Eintracht Frankfurt in May 2022
West Ham reached the Europa League semi-finals in 2022 and won the Europa Conference League last season. They also topped a group that included Freiburg this term to qualify automatically for the last 16.
Last season they won every game in Europe so never had to overcome a first-leg deficit, but they did manage it at this stage two years ago when they lost 1-0 at Sevilla before going through after extra time at London Stadium.
That Sevilla side looked a tougher opponent than Freiburg, who sit mid-table in the Bundesliga. So there's no need to panic for West Ham, who have won their last 10 European home games.
But they will have to improve their finishing on Thursday.
Bowen is their top scorer this season with 17 goals, but none in Europe, and he had chances to break that duck in Germany.
He had a shot saved from a tight angle and snatched at a volley from Kudus' cross.
Paqueta headed wide from a Kudus cross and Konstantinos Mavropanos did the same from James Ward-Prowse's corner. Kudus caused plenty of problems for the home defence and had an effort saved himself.
