Stadium: Quadra Central Round: 25 Ground: Clay
| French Open | 2023/05/24 09:50 | Juan Manuel Cerundolo v Hamad Medjedovic | 3-6,6-3,3-6 |
| French Open | 2023/05/22 11:30 | Juan Manuel Cerundolo v Zachary Svajda | 7-6,6-3 |
| Challenger Turin | 2023/05/17 20:35 | Juan Manuel Cerundolo v Andrea Collarini | 5-7,4-6 |
| ATP Rome | 2023/05/10 14:35 | Juan Manuel Cerundolo v Arthur Fils | 1-6,6-1,4-6 |
| ATP Rome | 2023/05/09 14:20 | Juan Manuel Cerundolo v Tomas Barrios Vera | 6-3,6-1 |
| ATP Rome | 2023/05/08 17:05 | Juan Manuel Cerundolo v Jelle Sels | 6-2,6-2 |
| Challenger Prague | 2023/05/02 08:30 | Juan Manuel Cerundolo v Dalibor Svrcina | 3-6,1-6 |
| ATP Madrid | 2023/04/25 15:55 | Alexander Shevchenko v Juan Manuel Cerundolo | 7-6,6-4 |
| ITF M25 Kiseljak | 2023/06/01 13:30 | Jerome Kym v Wilson Leite | 6-3,4-6,6-3 |
| ITF M25 Kiseljak | 2023/05/30 12:00 | Wilson Leite v Alejandro H Franco | 4-6,6-3,6-2 |
| Challenger Skopje | 2023/05/23 11:10 | Wilson Leite v Filip Cristian Jianu | 4-6,5-7 |
| Challenger Skopje | 2023/05/22 09:00 | Wilson Leite v Pedro Boscardin Dias | 7-6,6-4 |
| ITF M25 Reggio Emilia | 2023/05/17 07:30 | Wilson Leite v Sandro Kopp | 6-7,6-7 |
| Challenger Coquimbo | 2023/05/01 17:40 | Wilson Leite v Roman Andres Burruchaga | 3-6,3-6 |
| Challenger Buenos Aires | 2023/04/25 14:30 | Wilson Leite v Murkel Dellien | 3-6,2-6 |
| Challenger Buenos Aires | 2023/04/24 14:45 | Wilson Leite v Conner Huertas Del Pino | 3-6,5-7 |