Stadium: Central Round: 25 Ground: Hardcourt outdoor
| ITF - M15 Monastir | 2021/06/24 11:30 | Omni Kumar v Petros Tsitsipas | 6-1,6-2 |
| ITF - M15 Monastir | 2021/06/23 13:00 | Petros Tsitsipas v Jabari Stafford | 6-2,6-3 |
| 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 - M25 Bakio | 2021/06/29 08:55 | Hendrik Jebens v Inaki Montes-De La Torre | 6-7,3-6 |
| ITF M25 - Klosters | 2021/06/20 08:45 | Tomas Papik v Hendrik Jebens | 6-3,7-6 |
| ITF - M25 Angers | 2021/04/19 09:00 | Louis Dussin v Hendrik Jebens | 6-3,7-5 |
| ITF - M25 Angers | 2021/04/18 09:00 | Kalomm Panzo v Hendrik Jebens | 0-6,1-6 |
| ITF - M25 Meerbusch | 2021/04/12 11:00 | Hendrik Jebens v Milan Welte | 5-7,1-6 |
| ITF - M25 Meerbusch | 2021/04/11 13:30 | Emilien Voisin v Hendrik Jebens | 4-6,1-6 |
| ITF - M25 Biel | 2021/03/29 09:35 | Gijs Brouwer v Hendrik Jebens | 6-3,6-2 |
| ITF - M25 Trimbach | 2021/03/10 13:45 | Fabrizio Ornago v Hendrik Jebens | 7-6,6-3 |