Real Madrid's 2-0 loss to Liverpool on Wednesday set a new, unwanted record for the LaLiga giants and Champions League holders.
The defeat marked the first time Madrid have lost three games in a single group stage/league phase in the competition's history.
As Carlo Ancelotti's men struggled to find their footing, Kylian Mbappe and Mohamed Salah missed crucial penalty kicks that could have altered the outcome.
The loss drops Madrid to 24th in the standings, with just two wins and three losses so far.
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Liverpool's victory, on the other hand, marked a significant milestone. As the Reds celebrated their win, they ended an eight-game winless streak against the Spanish giants, with their last win coming in 2009 under Rafael Benitez.
Up next for Liverpool is the visit of Manchester City, and a win for Arne Slot's men will send them 11 points clear of the champions.
The Reds have lost just one game in all competitions this season, and are massive favourites to keep that run going against Pep Guardiola's men.