Djokovic, seeking a record sixth Indian Wells Masters crown, was pushed all the way in the opening set by American opponent Bjorn Fratangelo before he secured a 7-6, 6-2 win.
Djokovic is 0-2 against Kyrgios in their FedEx ATP Head2Head series, including a straight-sets loss in Indian Wells two years ago. Stan Wawrinka has a good record at the Indian Wells Open as he finished second at this tournament in 2017.
Venus Williams (USA) during her second round match as she defeated Petra Kvitova (not pictured) in the BNP Paribas Open at the Indian Wells Tennis Garden. It will be a tricky test for the youngster as Mladenovic had beaten her in Dubai. His season-low ranking of No. 22 is the lowest any player has been ranked in the same season they finished year-end No. 1.
"I learn the most when I lose matches, and honestly, it was great that I got to play her again because I was able to learn from the mistakes I did back then", Osaka said. "Had some moments where I let go of coaches that were maybe, for the outside people, not a logical step, but for me really the only step", Federer said.
"There were ups and downs in the first set. He was the one that was really aggressive and dictating the points from back of the court for entire first set".
"It was such a weird match", Kvitova said, calling it her worst of the year.
But Williams immediately broke back and Kvitova soon found herself serving to save the match.
"She has been playing so well and you never know what's going to come off her racket", a beaming Williams said in front of a fawning crowd as night fell on her native Southern California.
Williams, a three-time semifinalist at Indian Wells, is the oldest woman in the tournament at 38.
But she's learning to cope with the pressure of heightened expectations, and that includes thinking of her first ever title defense as a clean slate.
Cilic was also relatively comfortable, while Wawrinka was pushed before getting through in three sets. "He's got all the different options how to win points".
Eighth-seeded American John Isner raced into the third round with a 6-0, 6-2 victory over Australian qualifier Alexei Popyrin.
Bouchard save two match points late in the third set but she was unable to stop Flipkens, who claimed her second victory over the Canadian in as many days following Wednesday's doubles triumph.
Donna Vekic and Carla Suarez Navarro also made second-round exits.
"It seemed like I played even better when I was down".