Rangers were out of luck in Germany last night, going down 2-3 to Bundesliga Champions Stuttgart on Matchday Five of the UEFA Champions League.
Nevertheless, despite this setback, a draw at Ibrox against Olympique Lyon in two weeks time will send the Light Blues through to the last sixteen, a scenario everyone would have accepted back on Matchday One.
Manager Walter Smith made one change from Falkirk with Brahim Hemdani replacing Daniel Cousin.
It was the visitors who made the early running - Barry Ferguson´s sixth minute shot being blocked, the ball falling to DaMarcus Beasley who could not control the ball quickly enough.
Four minutes later Jean-Claude Darcheville shot into the side-netting from a Lee McCulloch pass.
Stuttgart began to impose themselves on the game - Cacau breaking through on goal in eighteen minutes only for Allan McGregor to block his effort with the visitors defence appealing for handball.
Sixty seconds later at the other end Kevin Thomson´s shot from a Darcheville cutback was deflected wide.
From the resultant Ferguson corner David Weir´s header was cleared off the line by Ludovic Magnin.
Rangers suffered a setback in 26 minutes when McCulloch limped off to be replaced by Charlie Adam. McCulloch was yellow-carded for his troubles for a foul on Roberto Hilbert, but as play carried on the Scot was taken out by Andreas Beck - an incident Slovenian Referee Darko Ceferin missed entirely.
Adam however produced the perfect response - he was on the park for just 59 seconds when he opened the scoring, turning the ball home from close range after Beasley´s corner was headed down by Carlos Cuellar.
The Bundesliga Champions responded immediately - Thomas Hitzlsperger´s 25-yard shot on the half-hour producing a fine one-handed save from McGregor, then nine minutes later the goalkeeper held Cacau´s volley from Beck´s cross.
As the interval approached the home side pressed for an equaliser - Sami Khedira slicing wide from an inswinging Magnin cross in 44 minutes.
However just when it appeared that Rangers had reached the sanctuary of the dressing-room with their lead intact Stuttgart equalised in first-half injury time. It was a bad goal to lose - Hitzlsperger´s corner finding the unmarked Pavel Pardo at the edge of the box, his drive across the face of goal being flicked home by Cacau.
It would prove to be a seminal moment in the match -for the home side came out with all guns blazing in the second-half.
Rangers suffered yet another injury blow four minutes after the restart when Beasley limped off following a clash with home goalkeeper Raphael Schafer, to be replaced by Steven Naismith.
The Germans were well on top - another Hitzlsperger corner finding Fernando Meira in 55 minutes, his header being held by McGregor.
The Ibox goalkeeper was however at fault seven minutes later when Pardo netted with a 25-yard drive from a Beck cutback.
Rangers were now right up against it - yet somehow levelled the scores in 69 minutes when Naismith streaked down the right, his cross breaking to Ferguson who coolly netted.
There was however to be one more twist in the tale - with Rangers pressing for the lead it was Stuttgart who scored again in 84 minutes when Ciprian Marica flicked home a Magnin cross.
There was no way back for Rangers - and afterwards Walter Smith reflected:
"It was dissappointing to lose. We lost a bad goal before half-time. Stuttgart started the second-half strongly. We lost the third goal when we were going for it near the end. It will be a big night at Ibrox in two weeks time."
STUTTGART Schafer; Beck, Fernando Meira, Delpierre, Magnin; Hilbert (Ewerthon 83), Pardo, Khedira (Da Silva 45), Hitzlsperger; Marica, Cacau (Tasci 88)
UNUSED SUBS Langer, Osorio, Meissner, Farnerud
RANGERS McGregor; Hutton, Weir, Cuellar, Papac; Beasley (Naismith 49), Ferguson, Hemdani, Thomson, McCulloch (Adam 26); Darcheviile (Cousin 82)
UNUSED SUBS Carroll, Boyd, Broadfoot, Whittaker
REFEREE Darko Ceferin (Slovenia)