Stadium: Center Court Round: 19 Ground: Clay
| Challenger Roseto | 2023/04/16 08:00 | Max Houkes v David Jorda Sanchis | 3-6,6-4,6-4 |
| ITF M25 Santa Margherita | 2023/04/12 10:35 | Goncalo Oliveira v Max Houkes | 6-2,1-6,6-3 |
| ITF M25 Santa Margherita | 2023/04/11 12:55 | Gian M Di Natale v Max Houkes | 3-6,3-6 |
| ITF M15 Antalya | 2023/04/07 11:45 | Sidane Pontjodikromo v Max Houkes | 6-4,7-6 |
| ITF M15 Antalya | 2023/04/06 11:10 | Danil Panarin v Max Houkes | 1-6,4-6 |
| ITF M15 Antalya | 2023/04/05 09:15 | Takuya Kumasaka v Max Houkes | 4-6,2-6 |
| ITF M25 Palmanova | 2023/03/26 09:00 | Stefano Travaglia v Max Houkes | 6-4,1-6,2-6 |
| ITF M25 Palmanova | 2023/03/25 09:30 | Max Houkes v Gianmarco Ferrari | 6-3,7-6 |
| Challenger Roseto | 2023/04/16 08:00 | Andrea Del Federico v Jacopo Berrettini | 3-6,0-6 |
| Challenger Barletta | 2023/04/06 10:20 | Jacopo Berrettini v Santiago Rodriguez Taverna | 2-6,2-6 |
| Challenger Barletta | 2023/04/05 08:00 | Dane Sweeny v Jacopo Berrettini | 1-6,6-7 |
| Challenger Barletta | 2023/04/03 09:50 | Salvatore Caruso v Jacopo Berrettini | 6-4,4-6,4-6 |
| Challenger Barletta | 2023/04/02 11:20 | Jacopo Berrettini v Filip Peliwo | 6-4,6-0 |
| Challenger Sanremo | 2023/03/26 10:45 | Kimmer Coppejans v Jacopo Berrettini | 6-3,6-2 |
| ITF M25 Portimao | 2023/03/15 14:40 | Jacopo Berrettini v Adria Soriano Barrera | 3-6,7-6,5-7 |
| Challenger Puerto Vallarta | 2023/03/08 03:30 | Jacopo Berrettini v Elmar Ejupovic | 4-6,6-7 |