Level, 3 wins each over 6 singles meetings since 2021. Last meeting on 04/04/2024 at Millennium Estoril Open - Estoril.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 04/04/2024 | Millennium Estoril Open - Estoril | Round 2 | clay | Ruud | 6-1 6-2 |
| 11/04/2023 | Monte-Carlo Rolex Masters - Monte-Carlo | Round 2 | clay | Ruud | 7-5 7-6(1) |
| 26/03/2023 | Miami Open - Miami | Round 3 | hard | Zandschulp | 3-6 6-4 6-4 |
| 10/05/2022 | Internazionali BNL d'Italia - Rome | Round 2 | clay | Ruud | 6-7(4) 6-2 6-4 |
| 29/04/2022 | BMW Open - Munich | Quarter-final | clay | Zandschulp | 7-5 6-1 |
| 01/09/2021 | U.S. Open - New York | Round 2 | hard | Zandschulp | 3-6 6-4 6-3 6-4 |
| clay | Zandschulp 1 - 3 Ruud |
| hard | Zandschulp 2 - 0 Ruud |
| 2024 | Zandschulp 0 - 1 Ruud |
| 2023 | Zandschulp 1 - 1 Ruud |
| 2022 | Zandschulp 1 - 1 Ruud |
| 2021 | Zandschulp 1 - 0 Ruud |
203 wins, 160 losses since 2021 (55.9%).
Last matches: D D D D V
254 wins, 121 losses since 2021 (67.7%).
Last matches: D V V V V
Level, 3 wins each over 6 singles meetings since 2021.
On 04/04/2024, at Millennium Estoril Open - Estoril (Round 2): Casper Ruud won 6-1 6-2.