| ITF M25 Torello | 02/28 10:40 | 25 | Merida Aguilar, Daniel v Ivanov, Simon Anthony | 2-6,6-4,6-2 | |
| ITF - M15 Monastir | 01/24 10:20 | 25 | Ivanov, Simon Anthony v Ilia Simakin | 2-6,0-6 | |
| ITF - M15 Monastir | 01/17 08:30 | 25 | Atlangeriev, Bekkhan v Ivanov, Simon Anthony | 7-6,6-0 | |
| ITF - M15 Monastir | 01/10 08:30 | 25 | Lilian Marmousez v Ivanov, Simon Anthony | 6-0,6-3 | |
| ITF M15 Madrid | 12/07 14:00 | 25 | Ivanov, Simon Anthony v Aleksandr Braynin | Retired | |
| ITF M25 Heraklion | 11/25 09:40 | 27 | Oleksandr Ovcharenko v Ivanov, Simon Anthony | 6-1,6-2 | |
| ITF M25 Heraklion | 11/24 10:30 | 26 | Ivanov, Simon Anthony v Tao Mu | Retired | |
| ITF M25 Heraklion | 11/22 14:05 | 25 | Ivanov, Simon Anthony v Svyatoslav Gulin | Retired | |
| ITF M15 Sozopol | 10/19 08:05 | 25 | Valentin Vanta v Ivanov, Simon Anthony | 6-3,6-2 | |
| ITF M15 Sozopol | 10/11 10:45 | 25 | Ivanov, Simon Anthony v Martyn Pawelski | 3-6,1-6 | |
| ITF M15 Sozopol | 10/05 07:00 | 25 | Frunza, Nicolae v Ivanov, Simon Anthony | 1-6,6-1,6-2 | |
| Challenger Banja Luka | 08/21 11:30 | 14 | Ivanov, Simon Anthony v Thiago Seyboth Wild | 4-6,0-6 | |
| ITF M15 Curtea de Arges | 08/13 08:55 | 28 | Valerio Aboian v Ivanov, Simon Anthony | 6-2,6-3 | |
| ITF M15 Curtea de Arges | 08/12 08:00 | 27 | Illya Beloborodko v Ivanov, Simon Anthony | 1-6,3-6 | |
| ITF M15 Curtea de Arges | 08/11 07:00 | 26 | Kristijan Juhas v Ivanov, Simon Anthony | Retired | |
| ITF M15 Curtea de Arges | 08/09 13:55 | 25 | Ivanov, Simon Anthony v Cezar Cretu | 6-2,7-6 | |
| ITF M15 Novi Sad | 08/04 08:00 | 26 | Florent Bax v Ivanov, Simon Anthony | 6-3,3-6,6-3 | |
| ITF M15 Novi Sad | 08/03 10:15 | 25 | Michalis Sakellaridis v Ivanov, Simon Anthony | 3-6,2-6 | |
| ITF M15 Novi Sad | 07/29 11:15 | 27 | Ivanov, Simon Anthony v Nicolas Zanellato | 6-3,4-6,2-6 | |
| ITF M15 Novi Sad | 07/28 10:15 | 26 | Ivanov, Simon Anthony v Kristijan Juhas | 6-4,7-5 | |
| ITF M15 Novi Sad | 07/27 10:00 | 25 | Ivanov, Simon Anthony v Nicolas Bruna | 6-7,7-5,6-2 | |
| ITF M15 Sofia | 07/09 09:15 | 28 | Vlad Andrei Dancu v Ivanov, Simon Anthony | 4-6,6-1,7-6 | |
| ITF M15 Sofia | 07/08 06:30 | 27 | Ivanov, Simon Anthony v Leonid Sheyngezikht | 6-2,6-3 | |
| ITF M15 Sofia | 07/07 08:55 | 26 | Ivanov, Simon Anthony v Viktor Markov | 6-4,7-5 | |
| ITF M15 Sofia | 07/06 08:30 | 25 | Ivanov, Simon Anthony v Matthew William Donald | 6-4,7-5 | |
| ITF M15 Wroclaw | 06/30 09:00 | 26 | Wojcik, Yann v Ivanov, Simon Anthony | Retired | |
| ITF M15 Wroclaw | 06/28 11:05 | 25 | Artem Podorozhnyi v Ivanov, Simon Anthony | 2-6,1-6 | |
| ITF M15 Budva | 06/05 08:30 | 29 | Damien Wenger v Ivanov, Simon Anthony | 6-4,6-4 | |
| ITF M15 Budva | 06/04 10:30 | 28 | Ivanov, Simon Anthony v Khumoyun Sultanov | 6-1,2-6,6-4 | |
| ITF M15 Budva | 06/03 08:30 | 27 | Ivanov, Simon Anthony v Tristan Schoolkate | 6-4,4-6,6-4 |