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Los Blancos booked their spot in the final four courtesy of a 3-1 aggregate victory over Liverpool in the quarter-finals, while Chelsea survived a late scare against FC Porto to beat the Primeira Liga giants 2-1 over two legs.
Real Madrid and Chelsea have only ever met three times down the years, and the Spanish side have failed to win any of those meetings - losing twice and drawing once to the Blues since 1971.
Chelsea lifted this trophy for the first and only time back in 2012, and look like they could go all the way this year - but they will need to take their chances against a Real team who win semi-finals without breaking a sweat.
The match will also see two of the founding members of the European Super League go head-to-head as proposals for the new competition lie in tatters.
Here, SPORTbible takes a look at everything you need to know ahead of the first Champions League semi-final.
Real Madrid vs Chelsea is scheduled for an 8pm (BST) kick-off on Tuesday, April 27.
The match will be held behind closed doors at the Estadio Alfredo Di Stefano in Madrid, Spain.
BT Sport 2 will be broadcasting the match and its subscribers will also be able to watch the match via the website or the BT Sport app.
While Real Madrid have enjoyed a spate of clean sheets recently, Chelsea have also recorded three shut-outs in a row before their journey to the Spanish capital.
The Blues have only conceded a trio of goals during this season's Champions League campaign so far, so expect a cagey affair in the first leg given the quality of both defences.
It wouldn't be a huge surprise if the tie was decided by a single goal over two legs, so the first 90 minutes may be short on chances.
Tuchel also has an FA Cup final to prepare for, but winning the biggest prize of them all in his first half-season at Stamford Bridge would go a long way to ensuring his stay in one of the most unforgiving jobs in the game.
Real Madrid are 13/10 to win, with Chelsea priced at 11/5 to come away with the victory. A draw is priced at 21/10.
Odds are correct at the time of publication and are subject to change.
Meanwhile, Federico Valverde remains in isolation after testing positive for coronavirus, and Zinedine Zidane could make do without three defenders as Sergio Ramos, Lucas Vazquez and Ferland Mendy keep each other company in the treatment room.
While Eden Hazard and Thibaut Courtois look to influence the game against their former club, Mateo Kovacic will not be reuniting with his former Blancos teammates, as Thomas Tuchel confirmed that a hamstring injury will keep the midfielder out of the first leg.
Aside from Kovacic, Chelsea have no other injury or suspension concerns for the first leg.
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