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