Round: 44 Ground: Hardcourt outdoor
| ITF M15 Heraklion | 2019/12/01 14:00 | Gianmarco Amatiste v Stephanos Schinas | 6-4,6-1 |
| ITF M15 Sharm El Sheikh | 2019/10/20 10:00 | Gianmarco Amatiste v Riccardo Tavilla | 6-7,4-6 |
| ITF M15 Sharm El Sheikh | 2019/10/13 10:00 | Davide Albertoni v Gianmarco Amatiste | 6-3,6-3 |
| ITF M25 Tavira | 2019/10/02 08:30 | Simon Carr v Gianmarco Amatiste | 6-2,6-1 |
| ITF M25 Tavira | 2019/10/01 10:20 | Goncalo Falcao v Gianmarco Amatiste | 2-6,3-6 |
| ITF M25 Tavira | 2019/09/30 11:30 | Gianmarco Amatiste v Francis Pare | 6-1,6-1 |
| ITF M15 Tabarka | 2019/07/22 07:30 | Lorenzo Brunetti v Gianmarco Amatiste | 6-4,6-3 |
| ITF M15 Tabarka | 2019/07/17 08:00 | Giovanni Calvano v Gianmarco Amatiste | 6-3,6-0 |
| ITF M15 Heraklion | 2019/12/01 14:00 | Frane Nincevic v Milen Ianakiev | 3-6,6-4,8-10 |
| ITF M25 Malibu | 2019/11/05 21:10 | Drew Baird v Milen Ianakiev | 6-3,6-3 |
| ITF M25 Malibu | 2019/11/04 18:00 | Chris Wettengel v Milen Ianakiev | 6-2,3-6,3-10 |
| ITF M25 Claremont | 2019/10/07 18:00 | Milen Ianakiev v Diego Nava | 6-4,3-6,8-10 |
| ITF M25 Chiswick | 2019/08/05 14:10 | Milen Ianakiev v Sizya Ernest Kivanda | 2-6,4-6 |
| ITF M25 Roehampton | 2019/07/29 08:30 | Milen Ianakiev v Sacha Modica | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/04 06:30 | Milen Ianakiev v Andrea Bessire | 4-6,2-6 |
| ITF M15 Plovdiv | 2019/06/03 10:00 | Milen Ianakiev v Cosmin Ontica | 1-6,6-4,10-6 |