Stadium: Court 1 Round: 25 Ground: Clay
| Challenger - Lissabon | 2021/09/28 11:15 | Robin Haase v Filippo Baldi | 6-4,4-6,6-4 |
| Challenger Braga | 2021/09/21 11:25 | Filippo Baldi v Taro Daniel | 2-6,6-4,0-6 |
| Challenger - Sevilla | 2021/09/06 17:15 | Bernabe Zapata Miralles v Filippo Baldi | 6-3,6-2 |
| Challenger - Como | 2021/08/30 09:00 | Filippo Baldi v Alexander Erler | 6-7,4-6 |
| Challenger - Como | 2021/08/29 12:55 | Filippo Baldi v Filip Cristian Jianu | 6-4,6-4 |
| US Open | 2021/08/24 19:30 | Joao Menezes v Filippo Baldi | 6-4,7-6 |
| Challenger - Verona | 2021/08/16 13:50 | Nino Serdarusic v Filippo Baldi | 6-3,6-2 |
| Challenger - Prag | 2021/08/09 14:30 | Filippo Baldi v Adrian Menendez-Maceiras | 3-6,6-7 |
| 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 |
| Davis Cup | 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 - Bolzano | 2021/08/04 08:25 | Petros Tsitsipas v Andrea Gola | 2-6,2-6 |