Never before had the Blancos failed to record a win in their first two outings in a competition they have dominated in recent seasons.
Real Madrid slumped to their worst-ever start in a Champions League campaign after failing to beat Club Brugge on Tuesday.
Zinedine Zidane's men were keen to turn a new page in Europe following their 3-0 humiliation at the hands of Paris Saint-Germain in their first outing of the 2019-20 season.
But they were immediately staring down the barrel when Emmanuel Dennis fired the visitors into the lead nine minutes in at the Santiago Bernabeu.
Dennis hit a second before half-time to widen the deficit, and Thibaut Courtois' withdrawal during the break due to an apparent injury only added another headache for the hosts.
But they managed to fight back to at least claim a point, with Sergio Ramos and Casemiro popping up to seal an agonising 2-2 draw that spared Real's blushes.
They may have avoided defeat, but Madrid could not help plumbing historic depths in Europe's most important club competition.
Never before had the Merengues started a Champions League campaign without a single win from their first two games since the tournament adopted its current format back in 1992-93.
There was cheer at least for Ramos, who once again proved his knack of scoring crucial goals for his side in Europe as he headed home with a goal that was confirmed after a check by VAR.
With seven headed goals in the Champions League the Spain enforcer has drawn level with John Terry as the record-holder in his position since 2003-04.
And Madrid will also be buoyed by the resolve shown in coming back from the brink.
Not since 2006-07 had the Blancos manage to overturn a two-goal deficit and claim a point in the Champions League, the last time coming against Dynamo Kiev in December 2006.
Next up for Zidane and Madrid will be Galatasaray, who welcome the most successful side in Champions League history to Istanbul on October 22.