| 30‑Oct‑2023 | Paris Masters | Hard | SF | 6 | 17 | Grigor Dimitrov [BUL] d. (7)Tsitsipas | 6-3 6-7(1) 7-6(3) | (ch) | 0.76 | 11.8% | 1.0% | 68.6% | 72.9% | 68.8% | 4/5 | 2:31 |
| 2‑Jan‑2023 | United Cup | Hard | RR | 4 | 28 | (1)Tsitsipas d. (16)Grigor Dimitrov [BUL] | 4-6 6-2 7-6(4) | | 0.97 | 12.6% | 1.1% | 75.8% | 77.8% | 52.2% | 8/9 | |
| 9‑May‑2022 | Rome Masters | Clay | R32 | 5 | 20 | (4)Tsitsipas d. Grigor Dimitrov [BUL] | 6-3 5-7 7-6(4) | | 1.03 | 11.2% | 4.7% | 68.2% | 72.6% | 55.9% | 4/6 | 2:37 |
| 2‑May‑2022 | Madrid Masters | Clay | R16 | 5 | 20 | (4)Tsitsipas d. Grigor Dimitrov [BUL] | 6-3 6-4 | (ch) | 2.38 | 20.4% | 0.0% | 69.4% | 85.3% | 80.0% | 0/0 | 1:18 |
| 18‑Apr‑2022 | Barcelona | Clay | R16 | 5 | 23 | (1)Tsitsipas d. (14)Grigor Dimitrov [BUL] | 6-1 6-4 | | 1.52 | 2.2% | 2.2% | 60.0% | 74.1% | 50.0% | 1/3 | 1:10 |
| 25‑Oct‑2021 | Vienna | Hard | R32 | 3 | 22 | (1)Tsitsipas d. Grigor Dimitrov [BUL] | 7-6(6) 6-4 | | 0.87 | 8.1% | 0.0% | 60.8% | 82.2% | 58.6% | 4/4 | 1:41 |
| 26‑Oct‑2020 | Vienna | Hard | R16 | 5 | 20 | Grigor Dimitrov [BUL] d. (3)Tsitsipas | 6-7(5) 6-4 6-3 | | 0.82 | 14.7% | 2.9% | 60.8% | 74.2% | 50.0% | 6/9 | 2:13 |
| 28‑Sep‑2020 | Roland Garros | Clay | R16 | 6 | 20 | (5)Tsitsipas d. (18)Grigor Dimitrov [BUL] | 6-3 7-6(9) 6-2 | | 1.44 | 3.0% | 0.0% | 62.0% | 71.0% | 71.1% | 3/3 | 2:26 |
