Stadium: Centre Court Round: 25 Ground: Clay
| Challenger Todi | 2023/08/14 12:05 | Samuel Vincent Ruggeri v Julian Ocleppo | 1-6,2-6 |
| Challenger Todi | 2023/08/13 12:25 | Federico Iannaccone v Julian Ocleppo | 1-6,6-4,3-6 |
| Challenger Cordenons | 2023/08/07 09:00 | Julian Ocleppo v Sebastian Dominko | 3-6,2-6 |
| Challenger San Benedetto | 2023/07/11 16:55 | Julian Ocleppo v Albert Ramos-Vinolas | 5-7,4-6 |
| Challenger San Benedetto | 2023/07/10 09:00 | Federico Zeballos v Julian Ocleppo | 2-6,2-6 |
| Challenger San Benedetto | 2023/07/09 09:00 | Benito Massacri v Julian Ocleppo | 2-6,2-6 |
| Challenger Troyes | 2023/07/02 08:00 | Emilien Voisin v Julian Ocleppo | 6-4,7-6 |
| Challenger Modena | 2023/06/27 10:30 | Julian Ocleppo v Salvatore Caruso | 4-6,6-3,0-6 |
| Challenger Cordenons | 2023/08/08 11:05 | Lorenzo Rottoli v Roman Andres Burruchaga | 5-7,6-3,6-3 |
| Challenger San Marino | 2023/07/31 15:00 | Roman Andres Burruchaga v Nerman Fatic | 3-6,6-3,3-6 |
| Challenger Verona | 2023/07/26 08:00 | Roman Andres Burruchaga v Benjamin Hassan | 5-7,6-4,6-7 |
| Challenger Trieste | 2023/07/20 14:45 | Roman Andres Burruchaga v Hugo Gaston | 3-6,6-4,0-6 |
| Challenger Trieste | 2023/07/18 11:20 | Roman Andres Burruchaga v Andrey Chepelev | 6-2,1-6,6-4 |
| Challenger Santa Fe | 2023/07/08 15:00 | Roman Andres Burruchaga v Adolfo Daniel Vallejo | 6-4,6-7,4-6 |
| Challenger Santa Fe | 2023/07/07 13:00 | Pedro Boscardin Dias v Roman Andres Burruchaga | 3-6,5-7 |
| Challenger Santa Fe | 2023/07/05 17:50 | Luciano Tacchi v Roman Andres Burruchaga | 6-7,3-6 |