West Ham drew a blank in the Black Forest as they slipped to a 1-0 defeat in the first leg of their Europa League last-16 meeting with Freiburg.
Jarrod Bowen and Lucas Paqueta missed golden opportunities to give the Hammers a lead to take back to the London Stadium next week.
But instead they will have to come from behind after they were hit by a late sucker punch from Freiburg substitute Michael Gregoritsch.
They were also denied what looked a clear penalty for handball in stoppage time after the referee refused to change his decision despite checking the pitchside monitor.
Nine months to the day since they lifted the Europa Conference League trophy in Prague, West Ham were back on their continental travels, and against familiar opponents.
Freiburg were the visitors to east London for the final group game just 84 days ago when a 2-0 win secured top spot for the Hammers.
West Ham also won 2-1 on their previous visit to south-west Germany in October, and travelled buoyed by back-to-back Premier League wins following a below-par start to the year.
Boss David Moyes, keen on another strong run in Europe, named his strongest line-up with cup goalkeeper Lukasz Fabianski replacing Alphonse Areola in the only change from Saturday’s victory at Everton.
West Ham were, as usual, happy to let their opponents have the ball but Freiburg gave them a scare when Roland Sallai’s through-ball split their defence.
Fortunately, Lucas Holer hit his shot into the ground and straight at Fabianski.
Moments later Bowen made a horrible mess of West Ham’s only chance of the first half.
The forward, who has not scored in Europe since his famous last-minute winner against Fiorentina in the Czech capital, peeled away at the far post to meet a Mohammed Kudus cross but badly fluffed his volley.
At the start of the second half Ghana winger Kudus cut inside Freiburg full-back only to curl his shot straight at keeper Noah Atubolu.
Bowen then scampered down the right wing and crossed for Paqueta, who also scuffed a volley wide.
A James Ward-Prowse corner should have been converted by Konstantinos Mavropanos but the centre-half’s header grazed the far post.
Paqueta then met another superb cross from Kudus but the finish, a simple header, again did not match the quality of the delivery, before Atubolu did well to tip Bowen’s curler wide.
Tomas Soucek also fired straight at Atubolu and Bowen just missed Aaron Cresswell’s cross before Freiburg struck.
A sloppy pass from Edson Alvarez gifted them possession and when Sallai took aim from the edge of the area, his wayward shot was tapped in by Gregoritsch.
Four minutes into stoppage time the ball struck the arm of Freiburg youngster Noah Weisshaupt in the area but after a long VAR check, referee Alejandro Hernandez checked the replay and stuck to his guns.
Nashville SC v San Jose Earthquakes: ‘A win would change everything’ - Godoy
Anibal Godoy insists that Nashville are already looking at their game against San Jose Earthquakes on Saturday as a must-win.
Nashville have won just once in the MLS this season and sit in 14th place in the Eastern Conference after a run of four without a win.
The Earthquakes, meanwhile, are bottom of the Western Conference having lost eight of their matches and recording just one win.
Godoy is aware of how their poor start to the season could affect their playoff hopes later down the line but is confident that Nashville can turn things around.
He said: “For us, it's an important week. It's a day we have to win, or we'll start to feel the pressure from other teams as they start to separate in the table.
“This league is long but if we want to get to the playoff you have to win games early on, especially at home.”
Liverpool agree compensation deal for Slot
Liverpool and Feyenoord have reached an agreement in principle over a compensation deal for Arne Slot to become the Reds’ manager next season, according to widespread Dutch media reports.
The Dutchman is reportedly poised to take over from Jurgen Klopp, who announced in January that he would be leaving the club at the end of the campaign.
Slot led Feyenoord to their second Eredivisie title last season after taking over the club in 2021.
It is believed that he topped the list of Liverpool’s favoured candidates due to his attacking playing style and ability to develop players.
Former Liverpool midfielder, Xabi Alonso, who led Bayer Leverkusen to their first Bundesliga title, and Sporting CP’s Ruben Amorim were also reported contenders to take over from Klopp.
Slot had already confirmed his interest in managing in the Premier League, both earlier this week and previously when he was linked to Tottenham in 2023.
QPR 4-0 Leeds United: Shock loss for Farke's men seals Leicester's promotion
QPR thrashed Leeds United 4-0 in the Championship on Friday, ensuring Leicester City booked their promotion straight back to the Premier League.
Ilias Chair was the star for the Hoops as he scored the opener and assisted two more goals to ensure QPR will stay in the Championship for another season.
Lucas Andersen, Lyndon Dykes and Sam Field also got their names on the scoresheet in an emphatic win for Marti Cifuentes' side.
Leeds' heaviest defeat of the season was a huge blow in the race for an automatic promotion spot, with Ipswich Town just one point behind them in third place with two games in hand going into their away clash against Hull City on Saturday.
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