Rangers' hopes of reaching the Champions League group stage are over after they were shocked by a second-half comeback from 10-man Malmo at Ibrox in the second leg of their third-round qualifier, losing 4-2 on aggregate.
Having lost the opening fixture 2-1 in Sweden, the Scottish champions were well placed to qualify when they led 1-0 at half-time in Glasgow through an Alfredo Morelos goal, with their chances boosted by Bonke Innocent's stoppage-time red card for the visitors.
But two goals from Antonio-Mirko Colak shortly before the hour mark turned the tie on its head, and Steven Gerrard's side were unable to respond.
Saturday’s 1-0 defeat by Dundee United in the Premiership at Tannadice on Saturday means Rangers have lost three games in a row.
They will now drop down to face either Kairat Almaty of Kazakhstan or Armenian champions Alashkert in the Europa League play-offs.
The constant din inside a packed Ibrox reached a crescendo when Kent slung in a cross from the left and Morelos knocked the ball past Malmo keeper Johan Dahlin with what looked like his back or shoulder.
The visitors came out of their shell towards the end of the first half, but seconds before the interval Innocent was shown a second yellow card by referee Slavko Vincic for a foul on Gers defender Connor Goldson, a decision which looked harsh.
Malmo took the game to Rangers at the start of the second half and Colak, who missed a first-half header, was clinical in the 53rd minute when set up by Veljko Birmancevic, firing past Allan McGregor from the angle.
And four minutes later he gathered a throw in, drifted past Leon Balogun and drilled in a low drive from 16 yards.
Malmo defended desperately under siege.
Morelos had a shot blocked then he headed wide and there were several more attempts which failed before Gerrard’s side ran out of inspiration, hope and then time before the boos rang round Ibrox.
