Sinner put some old demons to rest in overcoming American Ben Shelton 6-4, 7-6 (7/1), while Medvedev took out Greece’s Stefanos Tsitsipas 7-6 (7/3), 6-3.
Shelton, ranked 16, knocked Sinner out at the same stage last year, but on Wednesday the Italian looked confident from the start as he won in 88 minutes.
The US Open champion pulled ahead in the ninth game of the first set, breaking when Shelton hit long, then dominated the second set tiebreak.
“It was very tough, you don’t have so much control when you play against him… I just tried to stay strong mentally,” said Sinner.
World number five Medvedev and Tsitsipas were meeting for the 14th time.
The Greek started the second set strongly, breaking in the first game, but Medvedev broke in the fourth and eighth to progress.
Medvedev and Sinner have met four times this year already in the final stages of tournaments.
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