The Serbian, who is bidding to equal Rafael Nadal's record of 33 ATP Masters 1000 titles, will face the victor of other semi-final clash between world number two Rafael Nadal or reigning ATP Finals champion Stefanos Tsitsipas in the summit showdown.
That Saturday-night match turned into a memorable three-set victory over Nadal, which meant that Tsitsipas has now beaten each of the Big Three (it used to be a Big Four before Andy Murray's hip trouble) in the last nine months. "I knew what I had to do, it was clear to me, but I just wasn't capable of doing it".
But Tsitsipas, the Next Gen ATP finals champion, came back stronger in the decider with impressive court coverage and broke Nadal to take a 5-2 lead although he could not immediately serve out for the match. In 2019, though, the mix of this magic elixir has gone off. Nadal has played in three clay-court tournaments this season.
After starting slowly on clay last month after another knee injury, Nadal is hopeful of quick progress, but he has alluded to the fact that he could walk away if he cannot return to his best.
Nishikori and Wawrinka will meet in the third round on Thursday, an early showdown for two players that have reached 12 Grand Slam semi-finals between them.
"Emotionally it was very tough, it was one of my toughest wins", Tsitsipas said.
"I wasn't playing my best tennis after the Australian Open so I was looking to regain momentum", Djokovic told Sky Sports.
Tsitsipas was hoping to lift his third trophy this year, following the crowns he won in Estoril and Marseille.
"You just have to accept it and I have to accept it naturally".
"I feel happy with my performance, but at the same time, I feel empty", said Tsitsipas. I'll be able to try to win these tournaments that I was not able to win this year.
The seventh-ranked Dutch became the first woman to win the Madrid title without dropping a set. I trained around 5 pm & it was very hot but it was more windy, colder.
"He has the best backhand that I have ever seen in a human being", said Tsitsipas of his opponent.
"He deserved the victory, he played unbelievable", said the 20-year-old Greek finalist. He then followed that up with another hard fought win over Philipp Kohlschreiber of Germany on Tuesday.
Tsitsipas was playing his second Masters 1000 final after losing to Nadal in Toronto last August.
Defending champion Petra Kvitova defeated Caroline Garcia, 6-3, 6-3, to set up a quarterfinal match against Kiki Bertens.