Tottenham face an arduous task to keep their Champions League hopes alive after defeat at home by the highly impressive RB Leipzig in the first leg of their last-16 tie.
Spurs, now stripped of long-term injury victim Son Heung-min with a broken arm as well as Harry Kane, were beaten more convincingly than the scoreline suggests as the side lying second in the Bundesliga demonstrated their growing stature.
And it was only a masterclass from goalkeeper Hugo Lloris that gives Spurs hope for the second leg in Germany, keeping Leipzig at bay with a string of outstanding saves before he was beaten by Timo Werner's 58th-minute penalty.
Lloris turned Angelino's shot on to the post and saved from Werner inside the first minute, later denying the striker once more from point-blank range.
He was powerless to stop Werner's drilled spot-kick after Ben Davies fouled Konrad Laimer but kept Spurs in it with a crucial block from Patrik Schick.
Spurs finally forged chances of their own after the break, with Leipzig keeper Peter Gulacsi turning Giovani Lo Celso's free-kick on to the post and Lucas Moura heading over from close range - but it is advantage to Julian Nagelsmann's team.
The big question for Spurs and manager Jose Mourinho was how they would lay a glove on RB Leipzig after the blow of losing Son to a broken arm exacerbated the long-term absence of main marksman Kane.
And so it proved as, despite a much-improved second half, they could not apply consistent pressure to Leipzig, who will go into the second leg as firm favourites to reach the quarter-finals.
Spurs should not be written off after the heroics of last season but without Kane and Son it would be an outstanding feat if they were to overturn this deficit.
Mourinho at least had shining lights in goalkeeper Lloris and midfield man Lo Celso, the France keeper preventing Leipzig from reducing the second leg to little more than a formality.
It was an ominous sign that he was in frantic action inside the first minute and he can take credit for Leipzig not being out of sight already.
Lo Celso, meanwhile, showed his growing maturity as he drove Spurs forward, almost equalising with a fine 25-yard free-kick that was turned on to the post by the stretching Gulacsi.
It was, however, a night of frustration for Spurs - summed up by the sight of a stony-faced Dele Alli hurling a water bottle and a boot in the dugout after he was substituted.
Spurs must call on the Champions League spirit of last season to turn this last-16 tie around.
Werner was centre stage in the build-up to this match, with the 23-year-old striker being heavily linked with a summer move to Liverpool as one of the most coveted players in Europe.
And he demonstrated exactly why as the spearhead of this dangerous, talented RB Leipzig side who are currently threatening the established order in the Bundesliga.
Werner, operating on the flanks, is blessed with pace, control, awareness and is a natural finisher with 20 goals in the German top flight this season.
He was a constant threat and will have been disappointed not to put Leipzig in an even more commanding position as he had two first-half efforts saved by Lloris, the second of which he should have finished.
Werner never let his head drop, berating team-mates when the service was not swift enough, and showing vision when he wrong-footed the Spurs defence by stepping over Angelino's cross from which Schick forced another fine save from Lloris.
He will provide Leipzig's big threat in the second leg on 10 March - and will surely be at the centre of serious transfer interest from Europe's elite clubs this summer.
Tottenham manager Jose Mourinho: "I'm not worried with the 1-0 - we can go there and win. What worries me is that these are our players for the next however many matches.
"Moura was absolutely dead, Bergwijn was absolutely dead, Lo Celso was absolutely dead.
"We are really in trouble. If it was just this game I'd say 'no problem' but we have FA Cup and Premier League games.
"I know Lamela could only give us 20 minutes and I knew Ndombele could not play for 90 minutes. I tried to manage the pieces I had."
Tottenham goalkeeper Hugo Lloris: "I want to stay positive especially after what we saw in the last 20 minutes. There is a second leg and we have a chance. It's not the best result we could get.
"There is a lot of quality in Leipzig and they showed it today. Because of all the circumstances against us in the past few weeks and months we have to stay positive. Not to find excuses... we have to be ready to fight."
