Stadium: Court 2 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sozopol | 2021/09/14 14:00 | Yanaki Milev v Bogdan Ionut Apostol | 6-7,6-7 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/18 09:00 | Yanaki Milev v Plamen Milushev | 3-6,6-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/17 09:00 | Yurii Dzhavakian v Yanaki Milev | 4-6,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/16 06:00 | Vasil Kirkov v Yanaki Milev | 6-1,6-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/15 09:00 | Gorazd Srbljak v Yanaki Milev | 6-3,6-2 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/13 10:30 | Vladimir Popov v Yanaki Milev | 4-6,6-4,2-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/07/12 06:00 | Yanaki Milev v Aleksandr Braynin | 7-6,4-6,4-6 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/10 10:30 | Mick Lescure v Yanaki Milev | 4-6,6-3,5-3 |
| ITF M15 Ulcinj | 2021/09/22 10:05 | Gianmarco Ferrari v Matthew Romios | 6-3,7-5 |
| ITF M15 Ulcinj | 2021/09/14 08:00 | Felix Gill v Matthew Romios | 6-3,3-6,6-4 |
| ITF M15 Allershausen | 2021/09/02 09:00 | Manish Sureshkumar v Matthew Romios | 6-1,5-7,6-3 |
| ITF M15 Allershausen | 2021/09/01 09:00 | Aliaksandr Bulitski v Matthew Romios | 4-6,6-7 |
| ITF M25 Trier | 2021/08/24 10:00 | Matthew Romios v Mick Veldheer | 1-6,0-6 |
| ITF M25 Ueberlingen | 2021/08/17 12:55 | Tim Handel v Matthew Romios | 6-4,6-2 |
| ITF M25 Frankfurt am Main | 2021/08/12 11:15 | Matthew Romios v Lucas Gerch | 6-7,1-6 |
| ITF M25 Frankfurt am Main | 2021/08/11 09:00 | Roberto Ortega-Olmedo v Matthew Romios | 2-6,4-6 |