Big Sinner guy here but I just think the deficit is too great so I voted never. He played so well the last two wins against Meddy but the matches could have gone either way and the H2H is still 2-6. I think they’ll probably trade wins for a while, maybe Sinner gets 2 and Meddy 1, but I am not sure he will overtake the H2H.

Maybe in 6 years if Sinner keeps growing and Medvedev starts to decrease his level in 5 years, then the h2h might start to lopside in Sinner’s favour.
In the near future I can see Sinner win 50% of their matches but not recovering from a -4