Manchester City were knocked out of the Women's Champions League by Atletico Madrid for a second consecutive season after a 2-1 second-leg loss in Spain.
England captain Steph Houghton's first-half own goal and Atletico skipper Angela Sosa's close-range finish gave the hosts control in the last-16 tie.
Germany's Pauline Bremer pulled a goal back late on, but City had to avoid losing after the first-leg draw.
Defeat in Madrid was a third straight loss in all competitions for City.
Nick Cushing's side reached the semi-finals in 2016-17 and 2017-18 but were knocked out by Atletico in the last-32 stage in 2018-19 and came unstuck against the Spanish league winners again this term.
City knew they needed a score draw or better in Madrid to have any hope of reaching the quarter-finals, after a 1-1 first-leg draw in Manchester on 16 October, and they mounted late pressure but could not find an equaliser.
A fortnight to forget for the FA Cup winners
Since the first leg, City have lost at Manchester United and Arsenal in the League Cup and Women's Super League respectively, but were boosted by England striker Ellen White's return from injury.
On her first start for the club, White went close to getting a vital goal in Madrid but fired wide early on and was denied by a good low save from former Arsenal goalkeeper Sari van Veenendaal after the break.
Substitute Bremer gave City late hope when she swept home confidently after Megan Campbell's long throw had been knocked on towards her at the far post.
Jill Scott and Campbell both went close with headers for the visitors, but by then the damage had been done by Atletico's two goals, the first of which went in off the City and England skipper shortly before half-time.
Houghton inadvertently deflected in Ludmila da Silva's effort, with the ball ricocheting off the centre-back twice.
Atletico - for whom England's former Manchester City forward Toni Duggan played the full 90 minutes - raised their arms in celebration at full-time, having progressed despite being unseeded for the last-16 draw.
While the hosts celebrated, City's players sat on the floor in agony and frustration, with their European ambitions over for another campaign.
Britain's other remaining sides - English champions Arsenal and Scottish champions Glasgow City - both hold leads and have home advantage for their second legs on Thursday, against Slavia Prague and Brondby respectively.
Man City boss Nick Cushing: "It's disappointing. For the players and the staff, it will hurt them. But it happens in football.
"I thought we dominated the game. We were the better team, we just lacked that little bit of extra edge to go and score.
"We're in a difficult period at the minute. In football, sometimes you have these difficult moments and you just have to believe, keep working hard and come out of the other end.
"Today showed me that we've got enough quality and we're still a good team."
Atletico Madrid: Van Veenendaal, Robles, Aleixandri, Tounkara, Menayo, Duggan, Santos (Linari 90+2), Virginia, Sosa, Corral (Meseguer 75), Da Silva (Sampedro 81).
Subs not used: Gallardo, Strom, Ovdiychuk, Garcia
Man City: Roebuck, Bonner, Houghton, Campbell, Stokes (Bremer 83), Walsh, Scott, Weir, Hemp, Stanway (Lee 75), White (Beckie 63).
Subs not used: Benameur, Toland, Wullaert, Fidalgo