| 6‑May‑2024 | Rome Masters | Clay | R16 | 8 | 11 | (6)Tsitsipas d. (9)Alex De Minaur [AUS] | 6-1 6-2 | (ch) | 2.43 | 0.0% | 0.0% | 69.2% | 74.1% | 83.3% | 1/2 | 1:00 |
| 26‑Feb‑2024 | Acapulco | Hard | QF | 12 | 9 | (3)Alex De Minaur [AUS] d. (5)Tsitsipas | 1-6 6-3 6-3 | (ch) | 0.98 | 5.9% | 9.4% | 52.9% | 57.8% | 45.0% | 6/12 | 2:06 |
| 31‑Jul‑2023 | Los Cabos | Hard | F | 5 | 19 | (1)Tsitsipas d. (5)Alex De Minaur [AUS] | 6-3 6-4 | (ch) | 1.59 | 4.2% | 0.0% | 58.3% | 82.1% | 55.0% | 0/2 | 1:26 |
| 17‑Apr‑2023 | Barcelona | Clay | QF | 5 | 19 | (2)Tsitsipas d. (8)Alex De Minaur [AUS] | 6-4 6-2 | | 1.47 | 2.0% | 0.0% | 56.9% | 72.4% | 72.7% | 1/1 | 1:21 |
| 21‑Mar‑2022 | Miami Masters | Hard | R32 | 5 | 28 | (3)Tsitsipas d. (25)Alex De Minaur [AUS] | 6-4 6-3 | | 1.79 | 14.0% | 1.8% | 59.6% | 82.4% | 69.6% | 3/3 | 1:30 |
| 7‑Feb‑2022 | Rotterdam | Hard | QF | 4 | 34 | (1)Tsitsipas d. Alex De Minaur [AUS] | 6-4 6-4 | | 1.43 | 7.3% | 0.0% | 60.0% | 81.8% | 54.5% | 2/3 | 1:31 |
| 4‑Oct‑2021 | Indian Wells Masters | Hard | R16 | 3 | 27 | (2)Tsitsipas d. (22)Alex De Minaur [AUS] | 6-7(3) 7-6(3) 6-2 | | 1.19 | 6.6% | 0.9% | 51.9% | 65.5% | 64.7% | 2/5 | 2:43 |
| 19‑Apr‑2021 | Barcelona | Clay | R16 | 5 | 25 | (2)Tsitsipas d. (14)Alex De Minaur [AUS] | 7-5 6-3 | | 1.10 | 7.1% | 1.4% | 70.0% | 75.5% | 52.4% | 2/3 | 1:24 |
| 2‑Feb‑2021 | Atp Cup | Hard | RR | 6 | 23 | Tsitsipas d. Alex De Minaur [AUS] | 6-3 7-5 | | 1.35 | 6.1% | 1.5% | 57.6% | 73.7% | 64.3% | 3/4 | 1:37 |
| 28‑Oct‑2019 | Paris Masters | Hard | R16 | 7 | 18 | (7)Tsitsipas d. Alex De Minaur [AUS] | 6-3 6-4 | | 2.77 | 24.4% | 0.0% | 75.6% | 85.3% | 81.8% | 1/2 | 1:09 |
| 5‑Nov‑2018 | NextGen Finals | Hard | F | 15 | 31 | (1)Tsitsipas d. (2)Alex De Minaur [AUS] | 2-4 4-1 4-3(3) 4-3(3) | (ch) | 1.30 | 13.3% | 0.0% | 69.3% | 76.9% | 60.9% | 2/3 | 1:40 |
| 1‑Oct‑2018 | Tokyo | Hard | R16 | 15 | 38 | (5)Tsitsipas d. Alex De Minaur [AUS] | 6-3 5-7 6-1 | (ch) | 1.30 | 4.9% | 1.2% | 48.8% | 77.5% | 50.0% | 3/6 | 2:21 |
| 7‑Aug‑2017 | Portoroz CH | Hard | R32 | 168 | 184 | Tsitsipas d. Alex De Minaur [AUS] | 6-2 6-3 | | 1.53 | 5.7% | 9.4% | 60.4% | 84.4% | 42.9% | 0/1 | 1:06 |
| 5‑Jun‑2017 | Surbiton CH | Grass | Q1 | 205 | 240 | Alex De Minaur [AUS] d. Tsitsipas | 7-6(5) 6-1 | | 0.65 | 1.5% | 6.0% | 61.2% | 65.9% | 34.6% | 8/12 | 1:19 |
| 1‑May‑2017 | Istanbul | Clay | Q1 | 207 | 228 | (7)Tsitsipas d. Alex De Minaur [AUS] | 6-4 6-2 | | 1.76 | 3.9% | 3.9% | 51.0% | 76.9% | 72.0% | 2/2 | 1:21 |
