Stadium: Court 3 Round: 25 Ground: Clay
| 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 Appiano | 2019/08/06 09:30 | Federico Arnaboldi v Antonio Massara | 6-4,6-4 |
| ITF M25 Casinalbo | 2019/07/11 11:25 | Antonio Massara v Pedro Sakamoto | 7-6,2-6,4-6 |
| ITF M25 Casinalbo | 2019/07/10 07:00 | Antonio Massara v Remy Bertola | 1-6,7-5,6-3 |
| ITF M25 Santa Margherita | 2019/09/24 12:00 | Gian Marco Ortenzi v Filippo Giovannini | 6-0,6-3 |
| ITF M25 Santa Margherita | 2019/09/23 12:00 | Gian Marco Ortenzi v Erwin Troebinger | 1-6,7-6,10-3 |
| ITF M25 Santa Margherita | 2019/09/16 12:00 | Gian Marco Ortenzi v Petro Orlando Fellin | 3-6,4-6 |
| ITF M15 Piombino | 2019/08/26 14:40 | Augusto Virgili v Gian Marco Ortenzi | 7-6,4-6,4-10 |
| Challenger L'Aquila | 2019/08/19 08:00 | Andrea Vavassori v Gian Marco Ortenzi | 7-5,6-4 |
| ITF M15 Santa Cristina | 2019/08/16 08:30 | Gian Marco Ortenzi v Marco Bortolotti | 2-6,2-6 |
| ITF M15 Santa Cristina | 2019/08/15 08:00 | Federico Iannaccone v Gian Marco Ortenzi | 4-6,6-3,6-7 |
| ITF M15 Santa Cristina | 2019/08/14 11:45 | Gian Marco Ortenzi v Gabriele Bosio | 6-3,6-2 |