Stadion: Court 2 TC Avenue Round: 25 Ground: Clay
| ITF - M15 - Melilla | 2019/09/26 09:00 | Simon A Ivanov v Timofey Skatov | 3-6,2-6 |
| ITF - M15 - Melilla | 2019/09/24 11:30 | Jose Joaquin M Cisneros v Simon A Ivanov | 1-6,1-6 |
| ITF - M15 - Varna | 2019/09/13 08:55 | Juan Ignacio Galarza v Simon A Ivanov | 1-6,6-1,6-4 |
| ITF - M15 - Varna | 2019/09/12 09:20 | Luca Gelhardt v Simon A Ivanov | 3-6,1-6 |
| ITF - M15 - Varna | 2019/09/11 07:00 | Simon A Ivanov v Niklas Schell | 3-6,6-0,6-2 |
| ITF - M25 - Pozoblanco | 2019/08/08 17:40 | Simon A Ivanov v Konstantin Kravchuk | 3-6,6-7 |
| ITF - M25 - Pozoblanco | 2019/08/07 20:25 | Simon A Ivanov v Nicolas Alvarez Varona | 4-6,6-2,6-2 |
| ITF - M25 - Pozoblanco | 2019/08/06 16:00 | Simon A Ivanov v Alvaro Blanco Damea | 6-4,3-6,10-6 |
| ITF - M15 - Burgas | 2019/10/08 12:00 | Michael Gloeckler v Vladimir Filip | 6-0,6-2 |
| ITF - M15 - Burgas | 2019/10/07 11:00 | Martin Iliev v Vladimir Filip | 2-6,2-6 |
| ITF - M15 - Burgas | 2019/10/07 07:00 | Tolga Basriev v Vladimir Filip | 0-6,2-6 |
| ITF - M25 - Jounieh | 2019/10/03 13:00 | Adam Moundir v Vladimir Filip | 6-0,6-1 |
| ITF - M25 - Jounieh | 2019/10/02 17:40 | Vladimir Filip v Markos Kalovelonis | 4-6,6-4,6-3 |
| ITF - M25 - Jounieh | 2019/10/01 08:00 | Alexandre Peyrot v Vladimir Filip | 7-6,1-6,5-10 |
| ITF - M25 - Jounieh | 2019/09/29 08:50 | Kate Fakih v Vladimir Filip | 2-6,4-6 |
| ITF - M25 - Jounieh | 2019/09/25 15:30 | Laurynas Grigelis v Vladimir Filip | 6-1,6-3 |