Nine-man Rangers progressed to the group stage of the Europa League after a 1-1 draw at FC Ufa, with the Scottish Premiership side winning the play-off 2-1 on aggregate.
The visitors had appeared to be cruising towards a place in Friday’s draw after Ovie Ejaria’s brilliant ninth-minute opener at the Neftyanik Stadium.
However, after Dmitri Sysuev brought the hosts level just past the half-hour mark, both Alfredo Morelos (38) and Jon Flanagan (66) saw red as Rangers were forced to hang on in the second half.
The visitors made the perfect start to proceedings when Ejaria got an away goal that meant their opponents would need to score three times without reply to progress.
The ball fell to Ejaria in the box, although the on-loan Liverpool midfielder still had work to do to bend his shot around a defender and past a helpless Aleksandr Belenov, before nestling in the top right-hand corner of the net.
However, if Steven Gerrard thought the tie was over, he was much mistaken as FC Ufa hit back 13 minutes before the break.
A simple ball over the top released Sysuev down the right and the midfielder charged on, before drilling a low shot past Allan McGregor at his near post.
And if that was bad enough, then Rangers soon found themselves down to 10 men after a moment of madness from Morelos, who first got needlessly booked for kicking the ball away.
However, the Colombia forward then compounded matters by arguing the decision with referee Tobias Stieler, who wasted no time in brandishing a second yellow.
If Rangers can have had no complaints about Morelos’ dismissal, then they will feel slightly aggrieved about the second yellow given to Flanagan after the former Liverpool full-back was judged to have caught an opponent with his elbow while jumping for a header.
That meant the visitors had to play the final quarter of the match with just nine men, only for a combination of brilliant McGregor saves and wasteful finishing from the hosts to see them through
After the Europa league game, Rangers take on arch-rivals and Scottish Premiership champions Celtic at Parkhead in the first Old Firm derby of the new season on Sunday lunchtime, with the game live on Sky Sports Football.