Stadium: Court 1 Round: 26 Ground: Hardcourt outdoor
| ITF - Sozopol M15 | 2021/10/06 07:00 | Tim Handel v Nikolay Nedelchev | 6-4,6-4 |
| ITF - Pardubice M25 | 2021/09/23 12:45 | Maciej Rajski v Tim Handel | 5-7,6-4,7-5 |
| ITF - Pardubice M25 | 2021/09/22 08:00 | Tim Handel v Lucas Gerch | 7-6,7-5 |
| ITF - Pardubice M25 | 2021/09/21 09:30 | Tim Handel v Mark Havlicek | 7-5,6-1 |
| ITF - Pardubice M25 | 2021/09/20 08:00 | Tim Handel v Jan Jermar | 6-4,6-3 |
| ITF - Allershausen M15 | 2021/09/03 09:55 | David Jorda Sanchis v Tim Handel | 7-6,5-7,6-4 |
| ITF - Allershausen M15 | 2021/09/01 14:35 | Marko Topo v Tim Handel | 5-7,5-7 |
| ITF - Trier M25 | 2021/08/29 09:00 | Tim Handel v Louis Wessels | 6-2,6-4 |
| ITF - Sozopol M15 | 2021/10/06 07:00 | Simon A Ivanov v Nikola Keremedchiev | 6-1,1-6,6-3 |
| ATP Sofia | 2021/09/26 11:05 | Pedro Martinez v Simon A Ivanov | 7-5,6-1 |
| ATP Nur-Sultan | 2021/09/19 06:00 | Simon A Ivanov v Dmitry Popko | 2-6,3-6 |
| ITF - Sozopol M15 | 2021/09/16 08:00 | Simon A Ivanov v George Tsivadze | 7-6,6-0 |
| ITF - Sozopol M15 | 2021/09/15 09:30 | Simon A Ivanov v Dragomir Draganov | 6-2,6-4 |
| ITF - Ulcinj M15 | 2021/09/07 08:00 | Felix Gill v Simon A Ivanov | 6-3,5-7,7-6 |
| ITF - Ulcinj M15 | 2021/09/01 13:30 | Antonio Cayetano March v Simon A Ivanov | 7-6,6-1 |
| ITF - Bacau M25 | 2021/08/18 12:40 | Simon A Ivanov v Arthur Cazaux | 4-6,4-6 |