Stadium: Court 7 Round: 62 Ground: Clay
| ITF - Skopje M15 | 2021/05/31 09:30 | Max Houkes v Rrezart Cungu | 6-7,3-6 |
| ITF - Majadahonda M15 | 2021/05/05 09:25 | Max Houkes v Oriol Roca Batalla | 0-6,6-2,2-6 |
| ITF - Majadahonda M15 | 2021/05/03 14:00 | Max Houkes v Diego A B Sanchez | 6-1,1-6,10-5 |
| ITF - Majadahonda M15 | 2021/05/03 10:45 | Max Houkes v Marco De Rossi | 6-2,6-4 |
| ITF - Majadahonda M15 | 2021/05/02 12:00 | Tiago Cacao v Max Houkes | 7-6,3-6,11-13 |
| ITF - Meerbusch M25 | 2021/04/12 11:30 | Yvo Panak v Max Houkes | 3-6,7-5,10-8 |
| ITF - Antalya M15 | 2021/04/02 08:50 | Pol Martin Tiffon v Max Houkes | 6-4,6-4 |
| ITF - Antalya M15 | 2021/03/31 07:00 | Max Houkes v Nicolo Turchetti | 6-3,6-1 |
| ITF - Antalya M15 | 2021/04/26 07:00 | Fabrizio Andaloro v Simeon Terziev | 4-6,6-4,11-9 |
| ITF - Antalya M15 | 2021/04/25 07:00 | Credit Chaiyarin v Simeon Terziev | 3-6,1-6 |
| ITF - Antalya M15 | 2021/04/18 07:00 | Kristof Minarik v Simeon Terziev | 6-1,6-1 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/03 10:00 | Jules Marie v Simeon Terziev | 6-3,6-0 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/02 07:00 | Ilya Snitari v Simeon Terziev | 6-0,6-3 |
| UTR Pro Tennis Series Pazardzhik | 2021/04/01 07:00 | Yurii Dzhavakian v Simeon Terziev | 4-6,4-5 |
| UTR Pro Tennis Series Pazardzhik | 2021/03/29 09:00 | Simeon Terziev v Gergely Madarasz | 3-6,1-6 |
| ITF - Antalya M15 | 2021/03/08 10:00 | Stefan Palosi v Simeon Terziev | 6-3,6-0 |