Estádio: Court 2 Round: 25 Ground: Clay
| ITF - M15 Santa Cristina | 2019/08/13 07:00 | Maurizio Speziali v Gian Marco Ortenzi | 5-7,5-7 |
| ITF - M15 Santa Cristina | 2019/08/12 07:00 | Gian Marco Ortenzi v Noah Thurner | 6-2,6-2 |
| ITF - M15 Wetzlar | 2019/08/05 09:00 | Gian Marco Ortenzi v Tim Handel | 6-3,3-6,7-10 |
| ITF - M25 Pontedera | 2019/07/22 13:00 | Marco Miceli v Gian Marco Ortenzi | 6-2,6-4 |
| ITF - M15 Gubbio | 2019/07/16 08:00 | Giuseppe Tresca v Gian Marco Ortenzi | 6-0,6-4 |
| ITF - M15 Heraklion | 2019/05/29 11:45 | Peter Kobelt v Gian Marco Ortenzi | 6-3,6-2 |
| ITF - M15 Heraklion | 2019/05/28 07:00 | Christos Keisidis v Gian Marco Ortenzi | 4-6,4-6 |
| ITF - M15 Heraklion | 2019/05/27 07:00 | Omer Yeshaya v Gian Marco Ortenzi | 2-6,4-6 |
| Challenger - Manerbio | 2019/08/05 09:25 | Gabriele Bosio v Scott Griekspoor | 3-6,6-7 |
| ITF - M25 Bolzano | 2019/07/30 10:45 | Denis Yevseyev v Gabriele Bosio | 6-2,6-1 |
| ITF - M15 Tabarka | 2019/07/22 13:45 | Gabriele Bosio v Andrea Picchione | 1-6,2-6 |
| ITF - M15 Tabarka | 2019/07/22 07:30 | Gabriele Bosio v Ervin H Eminefendic | 2-6,6-4,10-7 |
| ITF - M25 Santa Margherita | 2019/05/01 15:05 | Lloyd Glasspool v Gabriele Bosio | 6-3,6-3 |
| ITF - M25 Santa Margherita | 2019/04/23 12:00 | Benjamin Pietri v Gabriele Bosio | 6-3,6-2 |
| ITF - M25 Santa Margherita | 2019/04/18 12:00 | Giovanni Fonio v Gabriele Bosio | 6-2,6-3 |
| ITF - M25 Santa Margherita | 2019/04/16 14:30 | Gabriele Bosio v Alexandar Lazarov | 6-1,7-6 |