Holders Manchester City are out of the Champions League following a penalty shoot-out defeat to Real Madrid in an epic encounter at the Etihad Stadium.
After a 1-1 draw on the night that left the teams tied 4-4 on aggregate, Antonio Rudiger scored the winning spot-kick after Bernardo Silva and Mateo Kovacic had their attempts saved to see the 14-time winners progress 4-3 in the shoot-out.
Elsewhere, a bullet header from Joshua Kimmich saw Bayern Munich win 1-0 in their Champions League quarter-final second leg, claiming a 3-2 aggregate victory and knocking Arsenal out of the competition.
The return leg did not quite have the drama of the first at the Emirates, where the game ended in a 2-2 draw, but the Germans took advantage of a moment of lax Arsenal defending.
Kimmich powered home his effort just after the hour to see the Gunners beaten, suffering another blow to their hopes of silverware this season after a 2-0 defeat to Aston Villa in the Premier League on Super Sunday