Stadium: Court 5 Round: 29 Ground: Clay
| ITF M15 Alaminos-Larnaca | 2023/04/29 08:00 | Sergey Fomin v Simon A Ivanov | 1-6,7-6,3-6 |
| ITF M15 Alaminos-Larnaca | 2023/04/28 07:00 | Elmer Moller v Simon A Ivanov | 5-7,6-4,6-7 |
| ITF M15 Alaminos-Larnaca | 2023/04/27 09:25 | Dragos N Cazacu v Simon A Ivanov | 2-6,2-6 |
| ITF M15 Alaminos-Larnaca | 2023/04/26 08:50 | Alexandros Skorilas v Simon A Ivanov | 6-2,4-6,1-6 |
| ITF M15 Antalya | 2023/04/22 07:30 | Dragos Nicolae Madaras v Simon A Ivanov | 6-1,1-6,7-5 |
| ITF M15 Antalya | 2023/04/21 07:20 | Marvin Moeller v Simon A Ivanov | 4-6,2-6 |
| ITF M15 Antalya | 2023/04/20 07:00 | Simon A Ivanov v Michel Hopp | 7-6,6-4 |
| ITF M15 Antalya | 2023/04/19 12:20 | Gabriel Donev v Simon A Ivanov | 6-7,4-6 |
| ITF M15 Alaminos-Larnaca | 2023/04/29 08:00 | Sebastian Prechtel v Guy Den Ouden | 6-3,4-6,3-6 |
| ITF M15 Alaminos-Larnaca | 2023/04/28 07:00 | Guy Den Ouden v Jonas Trinker | 7-5,6-4 |
| ITF M15 Alaminos-Larnaca | 2023/04/27 07:00 | Guy Den Ouden v Nicolas Parizzia | 7-5,6-0 |
| ITF M15 Alaminos-Larnaca | 2023/04/26 07:00 | Guy Den Ouden v Shinnosuke Hiramatsu | 6-2,6-1 |
| ITF M25 Loule | 2023/03/02 13:30 | Guy Den Ouden v Giovanni Fonio | 4-6,4-6 |
| ITF M25 Loule | 2023/03/01 13:20 | Goncalo Falcao v Guy Den Ouden | 4-6,6-4,1-6 |
| ITF M25 Loule | 2023/02/28 10:30 | Guy Den Ouden v Niels Visker | 2-6,7-5,10-2 |
| ITF M25 Loule | 2023/02/27 11:40 | Guy Den Ouden v Ian Luca Cervantes Tomas | 6-3,6-3 |