Rangers 1 CSKA Moscow 1 CSKA Moscow win 3-2 on aggregateRangers' hopes of joining Celtic in today's Champions League draw were snuffed out by a second-half Vagner Love strike on a night when the home side had to win to stay alive.
The result also means a loss of £8 million in revenue as well as prestige and Celtic will be aiming to inflict further pain on their rivals in the Old Firm derby at Parkhead on Sunday.
The task was to retrieve a 2-1 first-leg deficit, but the Russian champions were not to be denied.
The setback heaps more pressure onto the shoulders of manager Alex McLeish, who has yet to see his side keep a clean sheet in Europe in 14 attempts.
There was also a flash of controversy just before half-time when Nacho Novo netted with a fine strike that was disallowed because the whistle had already gone.
Now Rangers' name will appear in tomorrow's low-key UEFA Cup draw rather than the razzmatazz of today's Champions League selections.
Vagner inflicted the mortal blow on the hour mark, prodding home from inside the six-yard box.
Thompson and Andrews combined to conjure up the 87th-minute leveller.
RANGERS: Klos, Ricksen, Moore, Boumsong, Vignal, Arveladze, Hughes, Mladenovic (Andrews 81), Lovenkrands (Thompson 64), Prso, Novo. Subs Not Used: Graeme Smith, Malcolm, Khizanishvili, Vanoli, Ross. Booked: Novo. Goal: Thompson 88.
CSKA MOSCOW: Akinfeev, Berezoutski, Semberas, Ignashevich, Odiah, Zhirkov, Rahimic, Aldonin, Jarosik, Olic (Semak 78), Vagner Love. Subs Not Used: Mandrykin, Gusev, Ferreira, Kirichenko, Laizans, Berezutsky. Booked: Odiah, Semak. Goal: Vagner Love 61.
Referee: Wolfgang Stark (Germany).