Stadium: Hard Court 4 Round: 62 Ground: Hardcourt outdoor
| ITF M25 Heraklion | 2023/10/30 07:00 | Yan Sabanin v Graham Maassen | 6-4,6-4 |
| ITF M25 Heraklion | 2023/10/29 09:00 | Glauco Pinheiro Da Cruz Junior v Graham Maassen | 6-2,2-6,12-14 |
| ITF M15 Heraklion | 2023/10/25 08:10 | Adam Heinonen v Graham Maassen | 6-4,6-3 |
| ITF M15 Heraklion | 2023/10/24 06:30 | Graham Maassen v Alessandro Spadola | 6-4,6-2 |
| ITF M15 Heraklion | 2023/10/23 07:30 | Eero Vasa v Graham Maassen | 4-6,6-3,7-10 |
| ITF M15 Heraklion | 2023/10/16 06:30 | Graham Maassen v Ki Lung NG | 2-6,4-6 |
| ITF M15 Heraklion | 2023/10/15 07:00 | Stefan Cizelj-Zivkovic v Graham Maassen | 3-6,3-6 |
| ITF M15 Lakewood | 2023/07/03 17:00 | Dominique Rolland v Graham Maassen | 6-4,6-2 |
| ITF M25 Heraklion | 2023/10/29 09:00 | Mihail Ivanov v William Norton | 3-6,4-6 |
| ITF M25 Pazardzhik | 2023/10/04 06:55 | Mihail Ivanov v Nikola Kolyachev | 4-6,2-6 |
| ITF M25 Pazardzhik | 2023/10/02 12:25 | Mihail Ivanov v Mykyta Riepkin | 6-4,6-2 |
| ITF M25 Pazardzhik | 2023/09/27 09:50 | Nicholas David Ionel v Mihail Ivanov | 6-1,6-3 |
| ITF M25 Pazardzhik | 2023/09/25 10:00 | Mihail Ivanov v Shendrit Deari | 0-6,6-3,10-8 |
| ITF M25 Pazardzhik | 2023/09/25 07:00 | Mihail Ivanov v Adam Krischke | 6-2,6-0 |
| UTR Pro Sofia | 2023/09/09 09:30 | Sergo Sikharulidze v Mihail Ivanov | 6-2,4-6,5-3 |
| ITF M15 Pirot | 2023/09/05 09:30 | Mihail Ivanov v Alen Mujakic | 1-6,6-3,7-10 |