| UTR Pro Tennis Series Beograd | 2021/07/07 07:30 | Milanovic, Dusan v Lazov, Alexander | 1-6,6-4,4-6 |
| UTR Pro Tennis Series Beograd | 2021/07/06 09:00 | Milanovic, Dusan v Vukovic, Luka | 6-2,5-2 |
| UTR Pro Tennis Series Beograd | 2021/07/05 10:30 | Giacomo Revelli v Milanovic, Dusan | 6-3,1-6,6-7 |
| ITF M25 Belgrade | 2021/06/30 10:05 | Milanovic, Dusan v Cungu, Rrezart | 2-6,5-7 |
| ITF M25 Belgrade | 2021/06/29 08:40 | Leonid Sheyngezikht v Milanovic, Dusan | 6-3,4-6,10-12 |
| ITF M25 Belgrade | 2021/06/28 10:00 | Milanovic, Dusan v Noskin, Egor | 6-4,6-4 |
| ITF M25 Belgrade | 2021/06/27 09:00 | Niv, Benjamin v Milanovic, Dusan | 3-6,4-6 |
| ITF - M15 Brcko | 2021/05/21 06:55 | Milanovic, Dusan v Joao Lucas Reis da Silva | 4-6,4-6 |
| UTR Pro Tennis Series Beograd | 2021/07/08 12:00 | Khomich, Aleksei v Alex Kuperstein | 6-2,6-0 |
| UTR Pro Tennis Series Beograd | 2021/07/06 09:00 | Giacomo Revelli v Alex Kuperstein | 6-7,6-4,0-6 |
| UTR Pro Tennis Series Beograd | 2021/07/05 10:30 | Alex Kuperstein v Lazov, Alexander | 6-4,7-5 |
| UTR Pro Tennis Series California | 2021/05/22 15:00 | Hadigian, Eric v Alex Kuperstein | 3-6,5-6 |
| UTR Pro Tennis Series California | 2021/05/21 20:45 | Alexander Stater v Alex Kuperstein | 6-2,3-6,2-6 |
| UTR Pro Tennis Series California | 2021/05/20 15:00 | Ortlip, Joshua v Alex Kuperstein | 6-1,5-3 |
| UTR Pro Tennis Series California | 2021/05/19 19:30 | Josh Sheehy v Alex Kuperstein | 6-3,6-5 |
| UTR Pro Tennis Series California | 2021/05/17 16:30 | R Seggerman v Alex Kuperstein | 3-6,4-6 |