Level, 5 wins each over 10 singles meetings since 2022. Last meeting on 25/09/2026 at Laver Cup - London.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 25/09/2026 | Laver Cup - London | Round robin | indoor hard | Ruud | 6-7(4) 6-4 10-8 |
| 02/05/2025 | Mutua Madrid Open - Madrid | Semi-final | clay | Ruud | 4-6 5-7 |
| 25/03/2025 | Miami Open - Miami | Round 4 | hard | Cerundolo | 4-6 2-6 |
| 20/09/2024 | Laver Cup - Berlin | Round robin | indoor hard | Cerundolo | 4-6 4-6 |
| 31/07/2024 | Olympics - Paris | Round 3 | clay | Ruud | 6-3 5-4 |
| 01/11/2023 | Rolex Paris Masters - Paris | Round 2 | indoor hard | Cerundolo | 5-7 4-6 |
| 17/05/2023 | Internazionali BNL d'Italia - Rome | Quarter-final | clay | Ruud | 7-6(5) 6-4 |
| 20/04/2023 | Barcelona Open Banc Sabadell - Barcelona | Round 3 | clay | Cerundolo | 6-7(5) 3-6 |
| 13/07/2022 | Nordea Open - Bastad | Round 2 | clay | Cerundolo | 4-6 6-3 5-7 |
| 01/04/2022 | Miami Open - Miami | Semi-final | hard | Ruud | 4-6 1-6 |
| indoor hard | Ruud 1 - 2 Cerundolo |
| clay | Ruud 3 - 2 Cerundolo |
| hard | Ruud 1 - 1 Cerundolo |
| 2026 | Ruud 1 - 0 Cerundolo |
| 2025 | Ruud 1 - 1 Cerundolo |
| 2024 | Ruud 1 - 1 Cerundolo |
| 2023 | Ruud 1 - 2 Cerundolo |
| 2022 | Ruud 1 - 1 Cerundolo |
249 wins, 119 losses since 2021 (67.7%).
Last matches: D V V V D
220 wins, 146 losses since 2021 (60.1%).
Last matches: D V D V V
Level, 5 wins each over 10 singles meetings since 2022.
On 25/09/2026, at Laver Cup - London (Round robin): Casper Ruud won 6-7(4) 6-4 10-8.