The Serb, seeded 10th, will play the victor of Saturday's second semi-final between Roger Federer and David Goffin.
After more than two years since their past meeting in the semi-finals of the 2016 Australian Open, Djokovic and Federer are back for the 18th shared title match of their careers. I think it's very hard to win Masters 1000s.
"I've played five finals here", Djokovic said.
The Swiss, seeking his eighth title in OH, saved all five break points he faced against the German and moves on to a third-round matchup with Argentine Leonardo Mayer.
Rain wreaked havoc on Thursday's schedule, leading to several players having to take the court twice on Friday.
"In the beginning, sometimes OK, you take them and you're happier to have an easier day at work but not when the crowd's packed like this and looking for an epic match". After defeating Khachanov 7-6 (5), 3-6, 6-4, Čilić's winning streak in Cincinnati continued after defeating Spaniard Carreno-Busta 7-6 (7), 6-4 later that day. "And to go back on the court again against Raonic, who was serving 140-plus miles (per hour) from the first game, that got me going, for sure, from the beginning".
The opening game of the third set was delayed 22 minutes because of lightning.
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"I feel like I'm trying to defend my title from way back when", he said. It was very, very tiring, the second set, and I just think that I couldn't really find energy in the third one. I feel and I heard that it's completely different.
While Federer narrowly avoided an early exit, another high seed was sent packing, as number four Juan Martin del Potro fell to diminutive Belgian David Goffin 7-6 (5), 7-6 (4).
Djokovic is 14-2 in his career against Cilic, who won his lone Masters 1000 title at Cincinnati two years ago.
The 10th-seeded Serb squared the match as the day's second bout of major rain moved in.
Earlier Friday, world number two Federer, bidding for his eighth Cincinnati title, outlasted Leonardo Mayer of Argentina 6-1, 7-6 (6) in the third round.
"But all of that is not going to happen if I lose so I'll try everything I can and hope for the best". "I'm glad that in the important points I played aggressively - that was important today".
Keys next faces Aryna Sabalenka of Belarus, who upset French sixth seed Caroline Garcia 6-4, 3-6, 7-5.