| 29‑Jul‑2024 | Paris Olympics | Clay | QF | 2 | 11 | (1)Djokovic d. (8)Stefanos Tsitsipas [GRE] | 6-3 7-6(3) | (ch) | 1.20 | 7.5% | 1.3% | 71.3% | 64.9% | 56.5% | 4/6 | |
| 16‑Jan‑2023 | Australian Open | Hard | F | 5 | 4 | (4)Djokovic d. (3)Stefanos Tsitsipas [GRE] | 6-3 7-6(4) 7-6(5) | (ch) | 1.40 | 7.0% | 3.0% | 66.0% | 81.8% | 61.8% | 2/3 | 2:56 |
| 14‑Nov‑2022 | Tour Finals | Hard | RR | 8 | 3 | (7)Djokovic d. (2)Stefanos Tsitsipas [GRE] | 6-4 7-6(4) | (ch) | 1.27 | 4.8% | 3.2% | 69.8% | 81.8% | 73.7% | 1/1 | 1:38 |
| 31‑Oct‑2022 | Paris Masters | Hard | SF | 7 | 5 | (6)Djokovic d. (5)Stefanos Tsitsipas [GRE] | 6-2 3-6 7-6(4) | (ch) | 1.70 | 14.1% | 0.0% | 62.8% | 83.7% | 72.4% | 0/2 | 2:19 |
| 3‑Oct‑2022 | Astana | Hard | F | 7 | 6 | (4)Djokovic d. (3)Stefanos Tsitsipas [GRE] | 6-3 6-4 | (ch) | 2.38 | 2.1% | 0.0% | 79.2% | 86.8% | 80.0% | 0/0 | 1:15 |
| 9‑May‑2022 | Rome Masters | Clay | F | 1 | 5 | (1)Djokovic d. (4)Stefanos Tsitsipas [GRE] | 6-0 7-6(5) | (ch) | 1.73 | 11.3% | 1.9% | 69.8% | 81.1% | 56.3% | 1/2 | 1:36 |
| 31‑May‑2021 | Roland Garros | Clay | F | 1 | 5 | (1)Djokovic d. (5)Stefanos Tsitsipas [GRE] | 6-7(6) 2-6 6-3 6-2 6-4 | (ch) | 1.32 | 3.7% | 2.2% | 67.9% | 78.0% | 53.5% | 5/8 | 4:11 |
| 10‑May‑2021 | Rome Masters | Clay | QF | 1 | 5 | (1)Djokovic d. (5)Stefanos Tsitsipas [GRE] | 4-6 7-5 7-5 | | 1.20 | 3.6% | 5.4% | 69.6% | 69.2% | 44.1% | 9/14 | 3:16 |
| 28‑Sep‑2020 | Roland Garros | Clay | SF | 1 | 6 | (1)Djokovic d. (5)Stefanos Tsitsipas [GRE] | 6-3 6-2 5-7 4-6 6-1 | (ch) | 1.23 | 3.3% | 3.9% | 66.7% | 72.5% | 47.1% | 11/15 | 3:54 |
| 24‑Feb‑2020 | Dubai | Hard | F | 1 | 6 | (1)Djokovic d. (2)Stefanos Tsitsipas [GRE] | 6-3 6-4 | (ch) | 1.40 | 3.5% | 0.0% | 63.2% | 77.8% | 57.1% | 1/2 | 1:17 |
| 28‑Oct‑2019 | Paris Masters | Hard | QF | 1 | 7 | (1)Djokovic d. (7)Stefanos Tsitsipas [GRE] | 6-1 6-2 | (ch) | 2.33 | 11.9% | 0.0% | 69.0% | 79.3% | 76.9% | 0/0 | 0:58 |
| 7‑Oct‑2019 | Shanghai Masters | Hard | QF | 1 | 7 | (6)Stefanos Tsitsipas [GRE] d. (1)Djokovic | 3-6 7-5 6-3 | (ch) | 0.92 | 9.3% | 2.3% | 74.4% | 70.3% | 72.7% | 5/7 | 2:02 |
| 6‑May‑2019 | Madrid Masters | Clay | F | 1 | 9 | (1)Djokovic d. (8)Stefanos Tsitsipas [GRE] | 6-3 6-4 | (ch) | 1.43 | 3.4% | 0.0% | 67.8% | 77.5% | 57.9% | 0/0 | 1:32 |
| 6‑Aug‑2018 | Canada Masters | Hard | R16 | 10 | 27 | Stefanos Tsitsipas [GRE] d. (9)Djokovic | 6-3 6-7(5) 6-3 | (ch) | 0.71 | 11.3% | 4.1% | 57.7% | 73.2% | 61.0% | 8/10 | 2:17 |
