Stadium: Hard 20 Round: 62 Ground: Hardcourt outdoor
| ITF M15 Heráklion | 2023/11/22 14:25 | Matic Kriznik v Petros Tsitsipas | 6-3,3-6,6-1 |
| Challenger Helsinky | 2023/11/05 09:00 | Petros Tsitsipas v Alibek Kachmazov | 3-6,0-6 |
| The Boodles | 2023/07/01 16:30 | Alex Molcan v Petros Tsitsipas | 6-2,6-2 |
| Challenger Heilbronn | 2023/06/04 10:55 | Petros Tsitsipas v Vladyslav Orlov | 2-6,4-6 |
| ITF M15 Monastir | 2022/09/18 13:00 | Petros Tsitsipas v Lawrence Bataljin | 7-5,6-3 |
| Challenger Granby | 2022/08/21 18:50 | Petros Tsitsipas v Luke Saville | 4-6,2-6 |
| Challenger Lexington | 2022/07/31 20:35 | Petros Tsitsipas v Ryan Harrison | 1-6,4-6 |
| Challenger Trieste | 2022/07/17 13:00 | Luca Van Assche v Petros Tsitsipas | 6-0,6-1 |
| ITF M15 Heráklion | 2023/11/21 07:00 | Benjamin Pietri v Przemyslaw Michocki | 6-4,6-0 |
| ITF M15 Heráklion | 2023/11/20 12:00 | Przemyslaw Michocki v Richard Zusman | 6-0,6-3 |
| ITF M15 Heráklion | 2023/11/20 07:00 | Filip Krolo v Przemyslaw Michocki | 3-6,6-2,7-10 |
| ITF M15 Koszalin | 2023/09/05 07:30 | Anthony Wright v Przemyslaw Michocki | 2-6,6-1,10-7 |
| ITF M15 Koszalin | 2023/09/04 09:00 | Adam Majchrzak v Przemyslaw Michocki | 5-7,3-6 |
| ITF M15 Szczawno | 2023/08/27 07:00 | Dominique Graf v Przemyslaw Michocki | 2-6,6-3,10-3 |
| ITF M25 Poznaň | 2023/08/22 08:55 | Lukas Palovic v Przemyslaw Michocki | 6-1,3-6,10-6 |
| ITF M25 Poznaň | 2023/08/21 12:55 | Przemyslaw Michocki v Piotr Kusiewicz | 6-4,6-2 |