Rangers ' Champions League hopes were shattered as they crashed out of the competition at the hands of Malmo 2-1 on aggregate after being reduced to nine men in the second leg of their third-round qualifier in Sweden.
Steven Whittaker and Madjid Bougherra were both shown straight red cards, before Malmo's Ricardinho was also dismissed by Russian referee Vladislav Bezborodov on a night of drama at the Swedbank stadium.
Nikica Jelavic cancelled out Daniel Larsson's strike from last week's clash in Glasgow but it was Jiloan Hamad who had the final say, with Rangers forced to settle for a Europa League play-off spot instead of taking a step closer to joining Europe's elite in the Champions League group stages.
Benfica ensured its name will be in Friday's draw for the Champions League play-offs with a 3-1 aggregate win over Trabzonspor .
The Portuguese Liga runner-up had secured itself a 2-0 advantage in the first leg of their third-round qualifier last week, and further extended that lead in Turkey with Nolito's 20th-minute opener.
Paulo Henrique equalised on the night for Trabzonspor, but the Turkish side was unable to add to its tally and will instead take a place in the Europa League play-offs.
FC Twente could only manage a goalless draw in the return leg of its qualifier against FC Vaslui , but it was enough to send them through to the play-offs.
The Eredivisie club travelled to Romania with a 2-0 lead, and although Luuk de Jong wasted a couple of good chances for the visitors, Twente was still able to progress.
Rubin Kazan saw off the challenge of Dynamo Kiev with a 4-1 aggregate victory.
Holding a 2-0 advantage from the first leg, Vladimir Dyadyun fired Rubin in front after 19 minutes with Aleksei Medvedev adding another three minutes from time.
Oleh Gusev's last-minute goal for Dynamo was little more than a consolation.
FC Zurich beat 10-man Standard Liege 1-0 at home, to go through 2-1 n aggregate
Liege lost Yoni Buyens to a straight red card on 21 minutes, before Admir Mehmedi's winner just prior to the hour mark.
Goals from Marek Bakos, Daniel Kolar and Milan Petrzela saw Plzen edge a close encounter with Rosenborg 3-2 and claim a 4-2 aggregate victory.
Mikael Lustig and Rade Prica had twice given the Norwegian visitors the lead in the Czech Republic but it was unable to shut its opponents out.
Apoel Nicosia beat Slovan Bratislava 2-0 in Slovakia to advance by the same score on aggregate. Ailton and Gustavo Manduca scored the goals in the second half.
Sturm Graz progressed to the play-offs at the expense of Georgian champion Zestafoni with a 2-1 aggregate success, winning the second leg 1-0 thanks to Roman Kienast's 69th-minute strike.
Wisla Krakow built on its first-leg lead over Litex Lovech by beating the Bulgarians 3-1 in the return match and 5-1 on aggregate.
Maor Melikson scored twice for the Polish hosts, with the second goal coming from the penalty spot.
A last-minute goal from Luis Ibanez secured Dinamo Zagreb a 1-0 win over HJK Helsinki , with the Croatian side advancing 3-1 on aggregate.
Maccabi Haifa played out a 1-1 draw with Maribor but the Israeli side's 2-1 win in the opening leg was enough to carry them through.
Genk also made good use of a 2-1 first-leg lead as its return match with Partizan Belgrade finished 1-1.