| ITF M15 Sozopol | 09/15 09:30 | 25 | Ivanov, Simon Anthony v Dragomir Draganov | 6-2,6-4 | |
| ITF M15 Ulcinj | 09/07 08:00 | 25 | Felix Gill v Ivanov, Simon Anthony | 6-3,5-7,7-6 | |
| ITF M15 Ulcinj | 09/01 13:30 | 25 | March, Antonio Cayetano v Ivanov, Simon Anthony | 7-6,6-1 | |
| ITF M25 Bacau | 08/18 12:40 | 25 | Ivanov, Simon Anthony v Arthur Cazaux | 4-6,4-6 | |
| ITF M25 Bacau | 08/17 07:00 | 62 | Ivanov, Simon Anthony v Gheorghe Claudiu Schinteie | 6-3,6-1 | |
| ITF M25 Bacau | 08/16 10:30 | 62 | Ivanov, Simon Anthony v Mandocescu, Laurentiu | 6-3,6-2 | |
| ITF M15 Telavi | 08/05 06:30 | 27 | Ivanov, Simon Anthony v Tashbulatov, Dostanbek | 6-4,4-6,2-6 | |
| ITF M15 Telavi | 08/04 06:30 | 26 | Ivanov, Simon Anthony v Zura Tkemaladze | 7-5,6-1 | |
| ITF M15 Telavi | 08/03 04:30 | 25 | Denis Klok v Ivanov, Simon Anthony | Retired | |
| ITF M25 Telavi | 07/27 06:50 | 25 | Beibit Zhukayev v Ivanov, Simon Anthony | Retired | |
| ITF M15 Sofia | 07/08 07:00 | 26 | Hanwen Li v Ivanov, Simon Anthony | Retired | |
| ITF M15 Sofia | 07/07 10:45 | 25 | Ivanov, Simon Anthony v Miladinovic, Marko | 7-5,6-1 | |
| ITF M15 Novomoskovsk | 05/31 06:15 | 44 | Ivanov, Simon Anthony v Pujol Navarro, Bruno | 4-6,4-6 | |
| ITF M15 Novomoskovsk | 05/31 06:15 | 44 | Ivanov, Simon Anthony v Ilnytskyy, Svyatoslav | 6-1,6-3 | |
| ITF M15 Novomoskovsk | 05/30 06:15 | 44 | Ivanov, Simon Anthony v Lorenzo Vatteroni | 6-1,6-2 | |
| ITF M15 Novomoskovsk | 05/25 07:00 | 44 | Ivanov, Simon Anthony v Maulenov, Timur | 6-4,5-7,7-10 | |
| ITF M15 Novomoskovsk | 05/24 12:00 | 44 | Ivanov, Simon Anthony v Denis Constantin Spiridon | 7-6,6-1 | |
| ITF M15 Novomoskovsk | 05/23 08:00 | 44 | Ivanov, Simon Anthony v Leyton Rivera | 6-4,6-2 | |
| ITF M15 Cairo | 05/09 09:00 | 29 | Matheus P De Almeida v Ivanov, Simon Anthony | Retired | |
| ITF M15 Cairo | 05/08 11:05 | 28 | Ivanov, Simon Anthony v Oliver Crawford | 7-5,6-4 | |
| ITF M15 Cairo | 05/07 08:00 | 27 | Carr, Simon v Ivanov, Simon Anthony | 3-6,6-1,1-6 | |
| ITF M15 Cairo | 05/06 09:40 | 26 | Ivanov, Simon Anthony v Aidan Mchugh | 6-2,6-2 | |
| ITF M15 Cairo | 05/05 15:40 | 25 | Lorenzo Bocchi v Ivanov, Simon Anthony | 6-4,4-6,2-6 | |
| ITF M15 Cairo | 05/04 08:00 | 62 | Ivanov, Simon Anthony v Eduardo Ribeiro | 4-6,6-3,10-7 | |
| ITF M15 Cairo | 05/03 09:00 | 62 | Ivanov, Simon Anthony v Niccolo Catini | 6-2,6-1 | |
| ITF M15 Cairo | 05/02 09:00 | 62 | Ivanov, Simon Anthony v Guelfo Baldovinetti | 6-3,6-4 | |
| UTR Pro Tennis Series Pazardzhik | 04/04 10:00 | - | Dzhavakian, Yurii v Ivanov, Simon Anthony | 6-2,6-4 | |
| UTR Pro Tennis Series Pazardzhik | 04/03 11:30 | - | Dimitrov, Martin v Ivanov, Simon Anthony | 7-5,2-6,1-5 | |
| UTR Pro Tennis Series Pazardzhik | 04/02 08:30 | - | Dinko Dinev v Ivanov, Simon Anthony | 6-2,5-0 | |
| UTR Pro Tennis Series Pazardzhik | 04/01 07:00 | - | Juan Bautista Otegui v Ivanov, Simon Anthony | View |