Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Ulcinj | 2021/09/07 08:00 | Felix Gill v Ivanov, Simon Anthony | 6-3,5-7,7-6 |
| ITF M15 Ulcinj | 2021/09/01 13:30 | March, Antonio Cayetano v Ivanov, Simon Anthony | 7-6,6-1 |
| ITF M25 Bacau | 2021/08/18 12:40 | Ivanov, Simon Anthony v Arthur Cazaux | 4-6,4-6 |
| ITF M25 Bacau | 2021/08/17 07:00 | Ivanov, Simon Anthony v Gheorghe Claudiu Schinteie | 6-3,6-1 |
| ITF M25 Bacau | 2021/08/16 10:30 | Ivanov, Simon Anthony v Mandocescu, Laurentiu | 6-3,6-2 |
| ITF M15 Telavi | 2021/08/05 06:30 | Ivanov, Simon Anthony v Tashbulatov, Dostanbek | 6-4,4-6,2-6 |
| ITF M15 Telavi | 2021/08/04 06:30 | Ivanov, Simon Anthony v Zura Tkemaladze | 7-5,6-1 |
| ITF M15 Sofia | 2021/07/07 10:45 | Ivanov, Simon Anthony v Miladinovic, Marko | 7-5,6-1 |