Rangers were sent crashing out of the Champions League at the hands of Malmo.
The Gers had the chance to dine at Europe’s top table after winning the Scottish title for the first time since 2011.
However, they found the Swedes too strong over two legs in the penultimate round of qualifying.
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Rangers trailed 2-1 from the first leg, but a diving header by Alfredo Morelos from an inswinging cross from Ryan Kent on 23 minutes sent a packed Ibrox into a frenzy.
Steven Gerrard’s side went into half-time with a spring in their step after Malmo’s Bonke Innocent was sent off.
Being a man down did not deter Malmo, as Antonio-Mirko Colak scored twice in four minutes shortly after the restart to turn the contest on its head.
Malmo's reward for the 4-2 aggregate success is a clash with Ludogorets who got the better of Olympiacos on penalties.
Rangers will get a second shot at European football as they will drop into the Europa League play-offs.
Monaco eased into the final round of Champions League qualifying after wrapping up a comfortable aggregate win over Sparta Prague.
After a 2-0 win in the first leg, Monaco completed the job on home soil with goals from Gelson Martins, Aleksandr Golovin and Sofiane Diop sealing a 5-1 victory over the two legs.
Up next for Monaco is a clash with Shakhtar Donetsk for a place in the group stage after the Ukrainian side saw off Genk.
Bruma’s goal secured PSV Eindhoven a 1-0 win at FC Midtjylland, and a 4-0 aggregate success.
Joao Mario was on target in Benfica's win over Spartak Moscow, and the Portuguese side will take on PSV for a place in the group stage.
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