It was evident from the first shot of the match that Kyrgios was there to entertain as he toyed with Medvedev en route to wrapping up the three-set win.
Kyrgios started the match on serve and performed an underarm serve with his first effort – which he won the point from.
A plethora of similar deliveries and trick shots followed as the Australian moved into the next round, making light work of a difficult opponent.
However, it was a moment in the penultimate game of the match where Kyrgios was leading 5-2 and attempted a SABR (Sneak Attack By Roger).
The 24-year-old rushed towards the net from the baseline to return his opponent’s serve.
But unlike Federer, Kyrgios then turned around and bent over, as if taunting Medvedev to strike the ball at his backside – which he went down the line instead.
Amazon Prime commentator Mark Petchey picked up on the clever SABR move, but questioned what happened in the aftermath.
“Well he tried a kind of Federer stealth return – the SABR,” Petchey said.
“But then doing that, you would never get Roger reacting that way.”
After the match, Kyrgios says he plotted to use the underarm serve with fellow pro Frances Tiafoe.
“I was joking with [Frances] Tiafoe before the game saying I was going to do an underarm serve with the first shot and see what happens,” he said.
“When it worked it encouraged me to keep doing it. It was a lot of fun.
“I think it is a good tactic against people like him. He needs rhythm and I didn’t give him rhythm today.”
The victory over Medvedev was only Kyrgios’ second match on clay this year.
“I don’t really need to play much tennis to play good,” he added.
“I believe in myself every time I go out.
“I knew today was going to be a tough battle. Medvedev has been playing unbelievable tennis this past year.
“He is going to have an unbelievable future. He is very good.
“I knew if I served well I would come out on top.”