Holders Atletico Madrid have been knocked out of the Europa League following a 2-1 aggregate defeat to Rubin Kazan.
Despite a 1-0 win on the night in Russia, the defending champions have failed to make it past the last 32 of the competition due to a loss in the first leg of their tie.
The visitors started brightly as Radamel Falcao saw his effort tipped away by Rubin goalkeeper Sergey Ryzhikov.
Atletico continued to dominate for the remainder of the opening half, but they struggled to create many meaningful chances in front of goal.
Raul Garcia had two opportunities before the break, only to be denied by Sergey Ryzhikov with his first before seeing the second fly wide of the post.
The hosts burst into life on the hour as Jose Rondon's drive was pushed away by Sergio Asenjo, but Atletico were soon up the other end with Cristian Rodriguez and Falcao both wasting their attempts.
The away side applied plenty of late pressure and they were rewarded for their efforts in the 84th minute when Falcao converted Adrian Lopez's cross.
As Atletico pushed for a second, Rubin were reduced to 10 men when Cesar Navas was sent off for his reckless challenge on Saul.
However, the holders were unable to snatch another goal as Rubin held on for the win.
