Level, 3 wins each over 6 singles meetings since 2021. Last meeting on 28/04/2026 at Mutua Madrid Open - Madrid.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 28/04/2026 | Mutua Madrid Open - Madrid | Round 4 | clay | Ruud | 7-6(4) 6-7(2) 6-7(3) |
| 21/04/2024 | Barcelona Open Banc Sabadell - Barcelona | Final | clay | Ruud | 5-7 3-6 |
| 14/04/2024 | Monte-Carlo Rolex Masters - Monte-Carlo | Final | clay | Tsitsipas | 1-6 4-6 |
| 17/12/2022 | Mubadala World Tennis Championship | Semi-final | hard | Tsitsipas | |
| 13/08/2021 | Rogers Cup - Toronto | Quarter-final | hard | Tsitsipas | 1-6 4-6 |
| 06/05/2021 | Mutua Madrid Open - Madrid | Round 3 | clay | Ruud | 7-6(4) 6-4 |
| clay | Tsitsipas 1 - 3 Ruud |
| hard | Tsitsipas 2 - 0 Ruud |
| 2026 | Tsitsipas 0 - 1 Ruud |
| 2024 | Tsitsipas 1 - 1 Ruud |
| 2022 | Tsitsipas 1 - 0 Ruud |
| 2021 | Tsitsipas 1 - 1 Ruud |
256 wins, 122 losses since 2021 (67.7%).
Last matches: V V V D V
243 wins, 117 losses since 2021 (67.5%).
Last matches: D D V D V
Level, 3 wins each over 6 singles meetings since 2021.
On 28/04/2026, at Mutua Madrid Open - Madrid (Round 4): Casper Ruud won 7-6(4) 6-7(2) 6-7(3).