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West Ham will have to come from behind in Germany next week if they are to reach their first European final in 46 years after Eintracht Frankfurt secured a deserved first-leg advantage at London Stadium.
Jarrod Bowen came agonisingly close to snatching a draw for the hosts in stoppage time when his overhead kick from a Declan Rice cross bounced down off the crossbar.
But that would have been harsh on Frankfurt, who were a constant threat on the counter-attack and showed why they had won away at Real Betis and Barcelona already in the knockout stages.
The visitors had the perfect start when Ansgar Knauff scored inside the opening minute.
The Hammers did recover through Michail Antonio's 11th goal of the season - and his first in the Europa League since September - as he bundled home Kurt Zouma's nod down at the far post.
It was Frankfurt who got the winner when Daichi Kamada tapped home after Djibril Sow's low shot was turned into his path.
Until the dramatic finale, a Bowen shot that flicked off the outside of a post and Said Benrahma's dipping second-half effort that flashed narrowly wide were West Ham's most dangerous efforts.
It was a disappointing outcome for David Moyes' men, although having performed brilliantly in Lyon to reach the last four, they do have hope when they travel to Frankfurt for the return.
Bubbles burst inside a minute
The stadium announcer proclaimed it the biggest football game at this stadium in the decade since it was opened - even if West Ham only took residency four years later.
Nothing about the build-up suggested otherwise. The pre-match rendition of 'I'm Forever Blowing Bubbles' was raucous. The noise that followed it immense.
That it took less than a minute for Eintracht to hit the mute button was a crushing disappointment.
As they went on to prove, the visitors were a menace on the counter-attack.
Still, despite Rafael Borre being given too much space to turn inside the West Ham box, the situation seemed to be under control. But Pablo Fornals lost Knauff at the crucial time and as the cross floated to the far post, it was the German who had the momentum to knock it in.
The 20-year-old was a scorer in the first leg of Eintracht's memorable victory over Barcelona in the previous round and could easily have had another as the ball broke kindly from an Aaron Cresswell tackle but his shot on the turn went just over.
It was the start of a pattern, West Ham building patiently for little reward, Eintracht moving the ball quicker in response and threatening the home goal.
Defensive woes
Zouma's return from an ankle injury should have brought additional solidity to West Ham's defence.
As it turned out, it was their weak point.
Cresswell looked particularly unnerved by the early goal and while the flowing move that carried Eintracht into the penalty area for their second was eye-catching enough, the lack of a challenge was glaring.
Kamada was fortunate the rebound from Alphonse Areola's save fell kindly for him but, as the saying goes, you make your own luck.
Had the Japanese midfielder found the net when his curling shot flicked off Craig Dawson as the visitors threatened again, West Ham's hopes of getting through would have been virtually over.
As it happens, while Eintracht have been unbeaten away from home in this competition, they have only won once in five attempts at Waldstadion, although, admittedly, they are yet to lose, something West Ham have to change.
Player of the match
KamadaDaichi Kamada
with an average of 6.84
West Ham United
Squad number20Player nameBowen
Squad number9Player nameAntonio
Squad number41Player nameRice
Squad number22Player nameBenrahma
Squad number15Player nameDawson
Squad number28Player nameSoucek
Squad number3Player nameCresswell
Squad number8Player nameFornals
Squad number31Player nameJohnson
Squad number10Player nameLanzini
Squad number13Player nameAreola
Squad number4Player nameZouma
Eintracht Frankfurt
Squad number15Player nameKamada
Squad number23Player nameHauge
Squad number10Player nameKostic
Squad number29Player nameLindstrøm
Squad number19Player nameBorré
Squad number36Player nameKnauff
Squad number13Player nameHinteregger
Squad number17Player nameRode
Squad number8Player nameSow
Squad number1Player nameTrapp
Squad number21Player nameAche
Squad number18Player nameTouré
Squad number35Player nameTuta
Line-ups
West Ham
Formation 4-2-3-1
- 13Areola
- 31Johnson
- 15Dawson
- 4Zouma
- 3Cresswell
- 28Soucek
- 41Rice
- 20Bowen
- 10LanziniSubstituted forBenrahmaat 66'minutes
- 8Fornals
- 9Antonio
Substitutes
- 1Fabianski
- 5Coufal
- 7Yarmolenko
- 11Vlasic
- 16Noble
- 22Benrahma
- 24Fredericks
- 26Masuaku
- 33Král
- 35Randolph
- 42Alese
- 51Chesters
Frankfurt
Formation 3-4-2-1
- 1Trapp
- 35Silva Melo
- 13HintereggerBooked at 81mins
- 18Touré
- 36Knauff
- 8SowBooked at 79mins
- 17Rode
- 10Kostic
- 29LindstrømSubstituted forHaugeat 62'minutes
- 15Kamada
- 19BorréSubstituted forAcheat 90+3'minutes
Substitutes
- 7Hrustic
- 9Lammers
- 20Hasebe
- 21Ache
- 22Chandler
- 23Hauge
- 24da Costa
- 25Lenz
- 27Barkok
- 31Grahl
- 39Mendes Paciência
- 47Horz
Live Text
Match ends, West Ham United 1, Eintracht Frankfurt 2.
Second Half ends, West Ham United 1, Eintracht Frankfurt 2.
Substitution, Eintracht Frankfurt. Ragnar Ache replaces Rafael Borré.
Attempt missed. Tomas Soucek (West Ham United) header from very close range is high and wide to the left. Assisted by Pablo Fornals with a cross following a corner.
Corner, West Ham United. Conceded by Tuta.
Jarrod Bowen (West Ham United) hits the bar with a left footed shot from the centre of the box. Assisted by Declan Rice with a cross.
Corner, West Ham United. Conceded by Almamy Touré.
Attempt blocked. Jarrod Bowen (West Ham United) header from the centre of the box is blocked. Assisted by Saïd Benrahma with a cross.
Foul by Kurt Zouma (West Ham United).
Rafael Borré (Eintracht Frankfurt) wins a free kick in the attacking half.
Corner, West Ham United. Conceded by Ansgar Knauff.
Attempt blocked. Sebastian Rode (Eintracht Frankfurt) right footed shot from outside the box is blocked.
Martin Hinteregger (Eintracht Frankfurt) is shown the yellow card for a bad foul.
Jarrod Bowen (West Ham United) wins a free kick on the right wing.
Foul by Martin Hinteregger (Eintracht Frankfurt).
Djibril Sow (Eintracht Frankfurt) is shown the yellow card for a bad foul.
Tomas Soucek (West Ham United) wins a free kick in the defensive half.
Foul by Djibril Sow (Eintracht Frankfurt).
Attempt blocked. Daichi Kamada (Eintracht Frankfurt) right footed shot from the left side of the box is blocked. Assisted by Rafael Borré.
Attempt missed. Saïd Benrahma (West Ham United) right footed shot from the left side of the box is high and wide to the right. Assisted by Declan Rice.
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