Real Madrid has never failed to progress to the Champions League knockout stage in their history.
Despite Los Blancos progressing from all 32 of their UCL group stages since they were introduced in 1995, that record is under serious threat this season.
Carlo Ancelotti's side crashed to a 2-0 defeat at Liverpool on Thursday morning (AEDT) - their third loss in five UCL games to date.
Now Real face an uphill battle to reach the knockout stage, let alone be a contender for their 16th Champions League title.
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Real Madrid on the brink of historic Champions League exit
With three UCL match days remaining, Real Madrid sit 24th on the standings out of 36 teams in the competition.
This season's Champions League sees the top eight teams qualify directly to the next round, while the following 16 ranked clubs will playoff against each other, with eight sides advancing to meet the top eight in a round-of-16.
Real currently sit the final playoff position but face three tricky matches to finish the group phase against Atalanta (away), RB Salzburg (home) and Brest (away).
While RB Salzburg are struggling, Atalanta are one of only three unbeaten teams in the competition alongside Liverpool and Inter, and Brest have won three of their five matches so far.
A playoff position seems more realistic for Real, who in 24th position are four points behind eighth-placed Monaco in the direct qualification spots.
Even if Real make the playoffs for the round-of-16, they will still need to progress through that two-leg match to avoid missing Champions League knockout qualification for the first time ever.
You can follow Real Madrid's faltering Champions League campaign live on Stan Sport.
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