Borussia Dortmund squandered chance after chance, including a second-half penalty, before slumping to a 1-0 defeat at Benfica in their first-leg match of the Champions League's round of 16.
Kostas Mitroglou scored shortly after halftime and goalkeeper Ederson made some key saves afterward to help Benfica hold.
Pierre-Emerick Aubameyang missed the penalty in the 58th minute, when his shot was stopped by the Brazilian goalkeeper.
"That's only possible in football, to play this well and to still lose," Dortmund coach Thomas Tuchel said.
"Luckily, there's a return leg for such games. It is an extremely complicated result, but I am very proud of how we played tonight. Even though I am very disappointed, I am proud of how we presented ourselves."
Benfica will be looking to reach the quarter-finals for the second consecutive season in the second leg on March 8 in Germany.
Mitroglou broke the deadlock following a corner early in the second half after a header by defender Luisao, who was making his 500th appearance for Benfica.
Mitroglou's initial effort was parried by goalkeeper Roman Burki but the striker was able to bundle home the loose ball.
It was Benfica's only attempt on target the entire match.
Dortmund's attack had thrived in the group stage, setting the competition's all-time scoring record with 21 goals in six games, but they faltered in Lisbon even though the German side controlled possession throughout the game.
"We should have and could have taken more from this game. We put in a top performance, we created many chances,
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