Stadium: Court 6 Round: 25 Ground: Clay
| Challenger Skopje | 2023/05/22 09:00 | Drzewiecki, Karol v Obrad Markovski | 6-2,7-5 |
| Challenger Skopje | 2023/05/21 09:00 | Drzewiecki, Karol v Durguti, Besir | 6-2,6-1 |
| Challenger - Ostrava | 2023/04/23 14:35 | Drzewiecki, Karol v Filip Peliwo | 1-6,6-3,6-7 |
| Challenger Biel | 2023/03/20 13:45 | Drzewiecki, Karol v Kirill Kivattsev | 4-6,3-6 |
| Challenger Biel | 2023/03/19 17:30 | Ramkumar Ramanathan v Drzewiecki, Karol | 4-6,7-5,2-6 |
| Challenger - Concepcion | 2023/01/23 14:00 | Juan Bautista Torres v Drzewiecki, Karol | 6-1,2-6,6-2 |
| Challenger - Concepcion | 2023/01/22 15:30 | Drzewiecki, Karol v Yunseong Chung | 6-3,6-2 |
| Challenger Guayaquil | 2022/10/31 16:25 | Drzewiecki, Karol v Colin Markes | 4-6,6-4,6-7 |
| Challenger Coquimbo | 2023/05/05 18:40 | Joao Lucas Reis da Silva v Roman Andres Burruchaga | 6-2,6-4 |
| Challenger Coquimbo | 2023/05/04 18:40 | Santiago Rodriguez Taverna v Roman Andres Burruchaga | 5-7,1-6 |
| Challenger Coquimbo | 2023/05/03 14:00 | Murkel Dellien v Roman Andres Burruchaga | 2-6,2-6 |
| Challenger Coquimbo | 2023/05/01 17:40 | Wilson Leite v Roman Andres Burruchaga | 3-6,3-6 |
| Challenger - Buenos Aires | 2023/04/28 15:30 | Mariano Navone v Roman Andres Burruchaga | 6-3,7-6 |
| Challenger - Buenos Aires | 2023/04/27 19:20 | Roman Andres Burruchaga v Gustavo Heide | 6-1,6-2 |
| Challenger - Buenos Aires | 2023/04/25 16:30 | Tomas Farjat v Roman Andres Burruchaga | 2-6,1-6 |
| Challenger - Florianopolis | 2023/04/19 13:00 | Andrea Collarini v Roman Andres Burruchaga | 6-2,6-1 |