| 27‑May‑2024 | Roland Garros | Clay | QF | 1 | 7 | (7)Casper Ruud [NOR] d. (1)Djokovic | W/O | | | | | | | | | |
| 8‑Apr‑2024 | Monte Carlo Masters | Clay | SF | 1 | 10 | (8)Casper Ruud [NOR] d. (1)Djokovic | 6-4 1-6 6-4 | (ch) | 1.19 | 3.8% | 2.5% | 58.2% | 67.4% | 57.6% | 3/7 | 2:17 |
| 29‑May‑2023 | Roland Garros | Clay | F | 3 | 4 | (3)Djokovic d. (4)Casper Ruud [NOR] | 7-6(1) 6-3 7-5 | (ch) | 1.60 | 10.9% | 1.0% | 73.3% | 79.7% | 63.0% | 3/4 | 3:14 |
| 14‑Nov‑2022 | Tour Finals | Hard | F | 8 | 4 | (7)Djokovic d. (3)Casper Ruud [NOR] | 7-5 6-3 | (ch) | 1.75 | 16.4% | 0.0% | 70.9% | 84.6% | 68.8% | 0/0 | 1:32 |
| 9‑May‑2022 | Rome Masters | Clay | SF | 1 | 10 | (1)Djokovic d. (5)Casper Ruud [NOR] | 6-4 6-3 | (ch) | 1.34 | 2.0% | 2.0% | 64.7% | 69.7% | 66.7% | 0/1 | 1:42 |
| 15‑Nov‑2021 | Tour Finals | Hard | RR | 1 | 8 | (1)Djokovic d. (8)Casper Ruud [NOR] | 7-6(4) 6-2 | (ch) | 1.98 | 18.9% | 0.0% | 73.6% | 89.7% | 42.9% | 0/1 | 1:30 |
| 14‑Sep‑2020 | Rome Masters | Clay | SF | 1 | 34 | (1)Djokovic d. Casper Ruud [NOR] | 7-5 6-3 | (ch) | 1.30 | 15.2% | 1.3% | 67.1% | 69.8% | 61.5% | 7/8 | 2:11 |
