Rangers crashed out of the Champions League playoffs Wednesday with a 6-0 loss to Club Brugge that heaped pressure on manager Russell Martin, while Benfica advanced at the expense of Jose Mourinho’s Fenerbahçe.
Benfica and Fenerbahçe had drawn 0-0 in the first leg in Istanbul last week and their tie was ultimately settled by a single goal in the return in Lisbon, scored by Turkish international Kerem Aktürkoğlu late in the first half.
That made it a losing return to the Estadio da Luz for Mourinho, who was briefly Benfica coach at the start of his managerial career, a quarter of a century ago.
Benfica, who lost to Barcelona in the last 16 last season, join city rivals Sporting in Thursday's league phase draw, while Fenerbahçe have to settle for a place in the Europa League – they have not appeared in the Champions League proper since 2008/09.
Meanwhile, Glasgow giants Rangers traveled to Belgium right up against it after losing 3-1 at home in last week's first leg, when they conceded three times in the opening 20 minutes.
They never looked like turning the tie around as Club Brugge took the lead inside five minutes at the Jan Breydelstadion through Nicolo Tresoldi and found themselves five goals ahead on the night by halftime.
Rangers were reduced to 10 men in the eighth minute when Max Aarons was shown a straight red card for hauling down Christos Tzolis and denying the striker a clear run on goal.
The visitors duly collapsed as Tzolis struck the bar from distance before his corner was headed in by Hans Vanaken, who hit the woodwork with a brilliant volley soon after.
Joaquin Seys added a quickfire double before Aleksandar Stankovic – son of Inter Milan's 2010 Champions League winner Dejan – headed in the hosts' fifth of the night in first-half stoppage time.
Tzolis completed the rout early in the second half, wrapping up a 9-1 aggregate win for the Belgians.
The defeat matches Rangers' heaviest ever losing margin in a European game.
They will drop into the Europa League, while Martin's position appears in jeopardy with the Champions League debacle following a start to their domestic campaign which has seen them draw their first three Scottish Premiership matches.
Rangers' next game is a high-stakes derby at Ibrox this weekend against Celtic, who were ousted from the Champions League on penalties by Kazakhstan's Kairat Almaty in their play-off tie on Tuesday.
"The only thing you can do tonight is accept the pain, accept the humiliation," Martin told broadcaster TNT Sports.
"We have to heal and get stronger. We have to show a big response on Sunday."
Elsewhere, FC Copenhagen beat Swiss champions Basel 2-0 on the night thanks to second-half goals by Andreas Cornelius and Youssoufa Moukoko, from a penalty, to advance 3-1 on aggregate.
Qarabag of Azerbaijan beat Hungary's Ferencvaros 5-4 on aggregate despite a 3-2 second-leg loss at home in Baku.
Leandro Andrade and Abdellah Zoubir scored for Qarabag on the night, with Gabi Kanichowsky, Barnabas Varga from a penalty, and Alex Toth netting for the visitors.
