CSKA Moscow snatched a second-half equaliser to hold Bayer Leverkusen to a 1-1 draw on Tuesday and hand a boost to Champions League Group E rival Tottenham and Monaco.
Kevin Volland's first-half strike looked to have sealed all three points for the visitor at Arena CSKA, but a penalty from Bibras Natcho denied Bayer a victory and kept alive third-placed Tottenham's hopes of reaching the last 16.
The result means Leverkusen is just three points ahead of Spurs prior to its game with group leader Monaco, but CSKA's fate is sealed, as only a win would have given them a chance of progressing.
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Volland capped a strong start by Roger Schmidt's side when he fired low past Igor Akinfeev after only 16 minutes, ensuring that the Russia international's wait for a clean sheet in the competition extended to 38 matches.
CSKA had earlier come close through Aleksandr Golovin and saw a shot from Alan Dzagoev whistle off-target, but, despite some sustained pressure, had to wait until midway through the second half for another clear chance, when Golovin's effort was stopped just in time by Bernd Leno.
Leonid Slutsky's side gave itself some hope 15 minutes from time, when Natcho fired his penalty low past Leno following a clumsy foul from Benjamin Henrichs, and it got a stroke of luck when Volland rattled the post with 10 minutes to play.
But there was to be no winner in sub-zero conditions in Russia, meaning CSKA must now focus on scrapping for a Europa League spot, while Leverkusen could yet go through with a match to spare if Monaco defeats Spurs.
CSKA wasted two clear chances for a valuable early goal, Golovin shooting straight at Leno from close range, having earlier frozen when one-on-one with the goalkeeper, although Hakan Calhanoglu fired narrowly wide of the post to give the home side a scare.
It was a lesson CSKA appeared not to heed, however. On 16 minutes, Calhanoglu played a free-kick short to Kevin Kampl and he chipped the ball into the path of Volland, who had time to control and fire low past Akinfeev from 12 yards after beating the offside trap.
Dzagoev, back from a long-term hamstring injury, blasted inches over after a good turn in the area, but CSKA had the assistant's flag to thank for preventing it from falling further behind when Omer Toprak turned in a rebound from Calhanoglu's free-kick, only for Javier Hernandez to have strayed offside.
CSKA mounted some good pressure after the break, though 18-year-old striker Fedor Chalov was given negligible service on his Champions League debut and struggled against the robust pairing of Toprak and Jonathan Tah.
Leverkusen looked dangerous on the counter-attack, particularly through the positive runs of Julian Brandt, and Calhanoglu bent a free-kick agonisingly wide after the young Germany winger had been fouled on one such promising burst forward.
The visitor had looked comfortable but came within inches of conceding an equaliser with just over 20 minutes to play, however Leno just did enough to smother the ball on the line after Golovin's shot on the turn had bounced through his legs.
But with 15 minutes to play, CSKA found its lifeline. Henrichs' lunged to reach the ball, but could only crash into Mario Fernandes, allowing Natcho to sweep the ball into Leno's bottom-right corner from the spot.
Volland skipped inside the CSKA area and struck the base of the post with a fine curling shot, but that was as close to a winner as either side came in a frustrating final few minutes.
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