stadio: Center Court Round: 25 Ground: Hardcourt indoor
| Challenger Napoli | 2021/10/05 12:55 | Filippo Baldi v Petros Tsitsipas | 6-4,3-6,6-4 |
| Challenger Napoli | 2021/10/04 08:00 | Bogdan Ionut Apostol v Petros Tsitsipas | 6-3,6-2 |
| Challenger Sibiu | 2021/09/28 08:40 | Damir Dzumhur v Petros Tsitsipas | 6-2,6-0 |
| Coppa Davis | 2021/09/18 09:00 | Petros Tsitsipas v Ricardas Berankis | 1-6,3-6 |
| Challenger Cassis | 2021/09/05 12:45 | Ramkumar Ramanathan v Petros Tsitsipas | 6-4,6-4 |
| ITF M15 Oldenzaal | 2021/08/19 11:20 | Daniel De Jonge v Petros Tsitsipas | 6-2,6-2 |
| ITF M15 Oldenzaal | 2021/08/18 15:00 | Petros Tsitsipas v Gabriel Alejandro Hidalgo | 7-5,6-2 |
| Challenger - Meerbusch | 2021/08/08 12:05 | Nerman Fatic v Petros Tsitsipas | 6-1,7-6 |
| ITF M25 Amburgo | 2021/10/20 08:00 | Louis Wessels v Jeremy Jahn | 6-1,7-6 |
| ITF M25 Ueberlingen | 2021/08/18 10:10 | Jeremy Jahn v Alexander Cozbinov | 3-6,7-6,1-6 |
| ITF M25 Bolzano | 2021/08/03 13:50 | Andrea Gola v Jeremy Jahn | 4-6,6-2,6-3 |
| ITF M25 Denia | 2021/07/27 17:25 | Carlos Lopez Montagud v Jeremy Jahn | 6-4,6-2 |
| ITF M25 Gandia | 2021/07/21 16:00 | Jordi Mas De Ugarte v Jeremy Jahn | 6-4,6-3 |
| Challenger Amersfoort | 2021/07/12 09:00 | Jeremy Jahn v Johan Nikles | 2-6,3-6 |
| Challenger Amersfoort | 2021/07/11 11:40 | Jeremy Jahn v Arjun Kadhe | 6-2,6-7,6-4 |
| ITF M25 Marburg | 2021/07/06 16:40 | Alexander Donski v Jeremy Jahn | 6-2,6-2 |