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.
Bristol City Women 0-4 Man City Women: Hosts relegated as Fowler double inspires WSL leaders
Mary Fowler scored twice to set WSL leaders Manchester City on their way to a 4-0 rout of Bristol City, who suffered relegation as a result, on Sunday.
With Arsenal having drawn with Everton earlier in the day, Man City knew a victory would be enough to take the title race down to two teams.
That victory duly arrived in emphatic fashion, with all four of Man City's goals arriving in the second half.
Fowler's fantastic strike opened the scoring in the 62nd minute, with the Australia international doubling her tally soon after, paving the way for an Amy Rodgers own goal and Alex Greenwood's late header to seal a huge victory.
Arsenal are now out of the title race, with Chelsea - who have two games in hand on Gareth Taylor's team - the only side capable of catching Man City.
The Robins, meanwhile, will be playing in the second tier again next term.
Data Debrief: Bristol heading down with a whimper
Bristol City have failed to score in their last five games in the WSL, a run of 544 minutes without a goal.
They mustered just 0.09 expected goals (xG) to Man City's 3.4, with the visitors having now kept a clean sheet in nine of their 20 league games this season.
De Rossi demands more from 'tired' Roma ahead of crunch run
Daniele De Rossi acknowledged his Roma team may be tired, but he insisted they must not allow themselves to be embarrassed.
Roma fought back to draw 2-2 with last season's Serie A champions Napoli in a pulsating fixture on Sunday.
Tammy Abraham's late header secured a point for De Rossi's team, who took the lead through Paulo Dybala's penalty before going behind to goals from Matias Olivera and Victor Osimhen.
With Serie A set to have five teams in the Champions League next season, Roma occupy fifth spot with four matches remaining, but sixth-placed Atalanta are just two points behind with a game in hand.
There is also the small matter of a Europa League semi-final against Bundesliga champions Bayer Leverkusen on the cards over the coming weeks, and De Rossi set the stall out.
"We drew, it is not a result to throw away, but it is not the result or the performance that we wanted," Roma coach Daniele De Rossi told Sky Sports Italia.
"At times you can steal the ball off Napoli, but we then gave it back again too many times. Napoli had a lot of chances in the first half, we did better in the second, but we have to do better.
"Look, we are tired, but we cannot start thinking that we’re tired and that means we can be embarrassed in the final few weeks of the season."
Roma host Leverkusen on Thursday before taking on Juventus on May 5, with a crunch clash against Atalanta – who are also into the Europa League semi-finals – set to follow after the away leg against Xabi Alonso's team.
Key to a successful end to the campaign for Roma will be keeping Dybala fit. The Argentine has been involved in the joint-most goals (12) in Serie A since the turn of the year, scoring nine and setting up three, level with Juve's Dusan Vlahovic.
PSG's latest Ligue 1 title arrives as Monaco lose to Lyon
Paris Saint-Germain have been crowned as Ligue 1 champions after Lyon overcame Monaco 3-2 on Sunday.
A 4-1 midweek win over Lorient ensured that one more victory would be enough for Luis Enrique's team to get over the line, but PSG failed to get the job done themselves when they faced relegation-threatened Le Havre on Saturday.
That game was the 700th match of the QSI era at PSG, and the club's 1,900th in France's top flight.
However, PSG's wait to win their third straight title did not last long, as less than 24 hours later, Lyon – who will face the Parisians in the final of the Coupe de France at the end of May – came out on top in a topsy turvy encounter with second-placed Monaco.
Substitute Malick Fofana was the matchwinner for Lyon, and ultimately the player who handed the title to PSG.
Wissam Ben Yedder had put Monaco ahead in the opening minute, but quickfire goals from Alexandre Lacazette and Said Benrahma turned the match on its head before half-time.
Ben Yedder netted his second to restore parity on the hour mark, and thought he had sealed his hat-trick when he volleyed in from a free-kick, only to have strayed offside.
With only a win good enough for Monaco to stay in the fight, the visitors were then caught out in the 84th minute, with Fofana racing onto Lacazette's throughball and finishing calmly.
After a dismal start to the season, relegation looked a real possibility for Lyon, but they are now, with three games remaining, still in with a shout of qualifying for Europe.
PSG on the other hand now have 12 Ligue 1 titles to their name, with 10 of those coming under QSI's ownership. Aside from the COVID-impacted 2019-20 season, five of their last six league titles have been secured before the start of May.
It also means Luis Enrique remains in the running for a treble in his first season at the club, with PSG taking on Borussia Dortmund in the Champions League semi-finals next week.
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