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The Blues are looking to reach the biggest game in European club football for the third time - and Thomas Tuchel will be hoping to replicate their 2012 success when a mid-season change of manager proved catalyst for European glory.
Meanwhile, Madrid are seeking an astonishing 14th title and a third under their current manager Zinedine Zidane.
Here, SPORTbible takes a look at everything you need to know ahead of the big game.
Chelsea vs Real Madrid is scheduled for an 8pm (BST) kick-off on Wednesday, May 5.
It will be televised on BT Sport 2 and BT Sport Ultimate.
BT Sport subscribers will also be able to watch the match online via the website or BT Sport app.
Wednesday's second leg represents the fifth meeting between Real Madrid and Chelsea in Europe, with the Blues unbeaten in their previous four against the 13-time European champions.
Chelsea have never welcomed Los Blancos to Stamford Bridge before, as their three meetings with the Spanish side before this season came in the 1998 UEFA Super Cup final and the two-legged final of the 1971 European Cup Winners' Cup, both of which the Blues won.
Karim Benzema's goal in the first leg saw him go level with Raul in the all-time Champions League top goalscorer charts, and a 72nd European strike this week would see him become the outright fourth highest scorer in the tournament's history.
Chelsea's all-important away goal gives them a slight advantage going into this game, particularly when you consider how solid they have been at the back under Tuchel.
And Real cannot rely on their resilient, albeit depleted defence to pave a way to the Champions League final, as they simply have to go for goals at Stamford Bridge in order to book their spot in the showpiece event.
Chelsea are 6/5 to win, with Real Madrid priced at 12/5 to come away with the victory. A draw is priced at 9/4.
Odds are correct at the time of publication and are subject to change.
Mateo Kovacic is likely to remain out after suffering a setback in training, but Thomas Tuchel is hopeful of having Antonio Rudiger back after he missed Saturday's win over Fulham with a knock picked up in the first leg.
Mason Mount was forced off late in the Fulham clash with a back problem, with Tuchel explaining afterwards that the change was precautionary.
Eden Hazard could play a more prominent role for Madrid as his comeback from injury continued with a start against Osasuna on Saturday.
Manager Zinedine Zidane insists Marcelo will be available despite being called up for polling duty in a local election the day before the game.
Meanwhile, Sergio Ramos could return from injury, which would allow Real to ditch the back-three used in the first leg.
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