Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Santa Margherita | 2019/09/27 12:00 | Antonio Massara v Flavio Cobolli | 6-2,4-6,2-6 |
| ITF M25 Santa Margherita | 2019/09/26 12:00 | Antonio Massara v Alessandro Procopio | 6-2,6-1 |
| ITF M25 Santa Margherita | 2019/09/25 15:35 | Antonio Massara v Gian Marco Ortenzi | 6-4,6-1 |
| ITF M25 Santa Margherita | 2019/09/13 16:30 | Davide Galoppini v Antonio Massara | 6-2,6-0 |
| ITF M25 Santa Margherita | 2019/09/13 11:00 | Antonio Massara v Toby Martin | 4-6,6-3,7-6 |
| ITF M25 Santa Margherita | 2019/09/12 11:00 | Antonio Massara v Giulio Graziotti | 6-2,6-0 |
| ITF M15 Santa Cristina | 2019/08/15 11:20 | Antonio Massara v Federico Campana | 2-6,2-6 |
| ITF M15 Santa Cristina | 2019/08/13 12:45 | Antonio Massara v Mattia Frinzi | 6-3,6-1 |
| ITF M25 Santa Margherita | 2019/09/27 12:00 | Louis Wessels v Jacopo Berrettini | 1-6,4-6 |
| ITF M25 Santa Margherita | 2019/09/26 14:10 | Louis Wessels v Alessandro Ingarao | 6-7,6-1,6-3 |
| ITF M25 Santa Margherita | 2019/09/24 13:15 | Louis Wessels v Andrea Borroni | 6-4,6-1 |
| Challenger Szczecin | 2019/09/10 16:15 | Filip Kolasinski v Louis Wessels | 6-3,7-5 |
| ITF M25 La Marsa | 2019/09/08 09:30 | Louis Wessels v Bruno Santanna | 5-7,4-6 |
| ITF M25 La Marsa | 2019/09/07 09:30 | Guilherme Clezar v Louis Wessels | 6-1,3-6,3-6 |
| ITF M25 La Marsa | 2019/09/05 13:50 | Louis Wessels v Guy Orly Iradukunda | 6-3,6-1 |
| ITF M25 La Marsa | 2019/09/05 10:30 | Louis Wessels v Moez Echargui | 6-3,6-3 |