Stadium: Court 6 Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Heraklion | 2021/06/10 07:30 | Petros Tsitsipas v Yasha Zemel | 6-7,2-6 |
| ITF - M15 Heraklion | 2021/06/08 08:00 | Petros Tsitsipas v Ioannis Kountourakis | 6-1,7-6 |
| ITF - M15 Heraklion | 2021/06/03 09:00 | Billy Harris v Petros Tsitsipas | 4-6,6-0,7-6 |
| ITF - M15 Heraklion | 2021/06/02 08:20 | Petros Tsitsipas v Alec Deckers | 6-4,6-4 |
| ITF - M15 Heraklion | 2021/05/27 10:45 | Petros Tsitsipas v Daniel Cox | 6-4,0-6,1-6 |
| ATP - Marseille | 2021/03/09 17:55 | Alejandro Davidovich Fokina v Petros Tsitsipas | 6-0,6-2 |
| ITF - M15 Monastir | 2020/12/24 10:20 | Kaichi Uchida v Petros Tsitsipas | 6-3,6-2 |
| ITF - M15 Monastir | 2020/12/22 08:30 | Petros Tsitsipas v Oscar Moraing | 1-6,6-4,7-6 |
| ITF - M15 Monastir | 2021/06/13 08:00 | Jabari Stafford v Alec Beckley | 3-6,3-6 |
| ITF - M15 Monastir | 2021/05/04 10:30 | Jabari Stafford v Karlis Ozolins | 1-6,1-6 |
| ITF - M15 Monastir | 2021/04/25 11:30 | Jabari Stafford v Yuta Kikuchi | 1-6,1-6 |
| ITF - M15 Monastir | 2021/04/18 11:00 | Miguel Fernando Pereira v Jabari Stafford | 6-1,6-0 |
| ITF - M15 Cancun | 2020/03/08 14:30 | Jabari Stafford v Oscar Mesquida Berg | 0-6,0-6 |
| ITF - M15 Cancun | 2019/11/10 16:30 | Jabari Stafford v Kiranpal Pannu | 3-6,2-6 |
| ITF - M15 Cancun | 2019/09/15 14:30 | William Griffith v Jabari Stafford | 6-0,6-2 |
| ITF - M15 Cancun | 2019/09/11 15:20 | Jabari Stafford v Cristian Rodriguez | 4-6,5-7 |