Played: 6 | Jannik Sinner: 2 | Alexander Zverev: 4

2024 – Cincinnati, Semifinal – Sinner won 7-6(9), 5-7, 7-6(4)

2023 – US Open, Round of 16 – Zverev won 6-4, 3-6, 6-2, 4-6, 6-3

2022 – Monte Carlo, Quarterfinal – Zverev won 5-7, 6-3, 7-6(5)

2021 – US Open, Round of 16 – Zverev won 6-4, 6-4, 7-6(7)

2020 – Cologne, Semifinal – Zverev won 7-6(3), 6-3

2020 – Roland Garros, Round of 16 – Sinner won 6-3, 6-3, 4-6, 6-3