Stadium: Court 4 Round: 25 Ground: Clay
| ITF M15 Novomoskovsk | 2021/05/31 06:15 | Ivanov, Simon Anthony v Pujol Navarro, Bruno | 4-6,4-6 |
| ITF M15 Novomoskovsk | 2021/05/31 06:15 | Ivanov, Simon Anthony v Ilnytskyy, Svyatoslav | 6-1,6-3 |
| ITF M15 Novomoskovsk | 2021/05/30 06:15 | Ivanov, Simon Anthony v Lorenzo Vatteroni | 6-1,6-2 |
| ITF M15 Novomoskovsk | 2021/05/25 07:00 | Ivanov, Simon Anthony v Maulenov, Timur | 6-4,5-7,7-10 |
| ITF M15 Novomoskovsk | 2021/05/24 12:00 | Ivanov, Simon Anthony v Denis Constantin Spiridon | 7-6,6-1 |
| ITF M15 Novomoskovsk | 2021/05/23 08:00 | Ivanov, Simon Anthony v Leyton Rivera | 6-4,6-2 |
| ITF M15 Cairo | 2021/05/08 11:05 | Ivanov, Simon Anthony v Oliver Crawford | 7-5,6-4 |
| ITF M15 Cairo | 2021/05/07 08:00 | Carr, Simon v Ivanov, Simon Anthony | 3-6,6-1,1-6 |
| ITF M25 Belgrade | 2021/06/30 09:00 | Miladinovic, Marko v Gorazd Srbljak | 3-6,4-6 |
| ITF M15 Skopje | 2021/06/09 09:10 | Joncour, Ronan v Miladinovic, Marko | 7-6,6-4 |
| ITF M15 Skopje | 2021/06/02 13:20 | Miladinovic, Marko v Oscar Moraing | 6-7,0-6 |
| ITF - M15 Prijedor | 2021/05/13 10:05 | Peter Fajta v Miladinovic, Marko | 5-7,6-3,7-6 |
| Belgrade, Serbia | 2021/04/18 13:30 | Miladinovic, Marko v Taro Daniel | 1-6,2-6 |
| Challenger Belgrade | 2021/04/12 10:00 | Taro Daniel v Miladinovic, Marko | 6-1,7-5 |
| ITF - M15 Antalya | 2021/03/24 07:30 | Hong, Seong Chan v Miladinovic, Marko | 6-2,6-4 |
| ITF - M15 Antalya | 2021/03/17 09:25 | Pedro Vives Marcos v Miladinovic, Marko | 6-2,6-3 |