Stadium: Court 3 Round: 25 Ground: Clay
| ITF M25 Pazardzhik | 2023/09/28 07:00 | Nicholas David Ionel v Simon A Ivanov | 6-0,6-1 |
| ITF M25 Pazardzhik | 2023/09/26 07:00 | Dragos Constantin Ignat v Simon A Ivanov | 2-6,2-6 |
| ITF M15 Pirot | 2023/09/08 08:00 | Simon A Ivanov v Peter Fajta | 2-6,6-7 |
| ITF M15 Pirot | 2023/09/07 07:30 | Simon A Ivanov v Erik Arutiunian | 7-6,4-6,6-0 |
| ITF M15 Pirot | 2023/09/06 07:30 | Simon A Ivanov v Marco Furlanetto | 3-6,7-6,7-5 |
| ITF M15 Kursumlijska Banja | 2023/08/29 12:20 | Simon A Ivanov v Giannicola Misasi | 6-7,3-6 |
| ITF M15 Targu Jiu | 2023/08/18 07:00 | Juan Pablo Paz v Simon A Ivanov | 6-3,6-7,6-4 |
| ITF M15 Targu Jiu | 2023/08/17 07:55 | Calin Manda v Simon A Ivanov | 3-6,6-4,3-6 |
| ITF M25 Pazardzhik | 2023/09/28 11:15 | Stefanos Sakellaridis v Nikola Kolyachev | 4-6,4-6 |
| ITF M25 Pazardzhik | 2023/09/26 08:30 | Stefanos Sakellaridis v Viktor Kirov | 6-2,6-2 |
| ATP Zhuhai | 2023/09/19 03:00 | Stefanos Sakellaridis v Luke Saville | 5-7,7-6,4-6 |
| Challenger Guangzhou | 2023/09/11 04:30 | Stefanos Sakellaridis v Arjun Kadhe | 3-6,1-6 |
| Challenger Zhangjiagang | 2023/08/31 04:40 | Stefanos Sakellaridis v Yusuke Takahashi | 3-6,1-6 |
| Challenger Zhangjiagang | 2023/08/29 10:05 | Evan Zhu v Stefanos Sakellaridis | 5-7,6-7 |
| Challenger Zhuhai | 2023/08/25 06:25 | Stefanos Sakellaridis v Arthur Weber | 6-4,4-6,2-6 |
| Challenger Zhuhai | 2023/08/24 04:40 | Stefanos Sakellaridis v Yi Zhou | 6-1,7-6 |