Stadium: Court 4 Round: 54 Ground: Hardcourt indoor
| ITF M15 Danderyd | 2023/09/18 13:30 | Simon Freund v Rafael Ymer | 6-1,6-2 |
| ITF M15 Vejle | 2023/07/24 12:00 | Simon Freund v Henrik Bladelius | 6-1,6-1 |
| ITF M15 Kalmar | 2023/05/16 12:00 | Simon Freund v Lewie Lane | 6-7,3-6 |
| ITF M25 Varnamo | 2023/05/11 08:15 | Dragos Nicolae Madaras v Simon Freund | 6-1,6-4 |
| ITF M25 Varnamo | 2023/05/10 08:10 | Simon Freund v Yan Sabanin | 6-0,6-0 |
| ITF M15 Antalya | 2023/04/24 09:05 | Simon Freund v Radovan Michalik | 2-6,0-6 |
| ITF M15 Antalya | 2023/04/17 12:35 | Konstantin Zhzhenov v Simon Freund | 1-6,6-2,10-2 |
| ITF M15 Antalya | 2023/04/16 07:00 | Maximilian Figl v Simon Freund | 6-1,2-6,5-10 |
| ITF M15 Danderyd | 2023/09/18 13:30 | Alfons Ridstrom v Drew Van Orderlain | 5-7,3-6 |
| ITF M15 Huntsville | 2023/05/22 14:00 | Vincent Rettke v Drew Van Orderlain | 6-4,6-1 |
| ITF M25 Varnamo | 2023/05/09 08:15 | Andrea Gola v Drew Van Orderlain | 7-6,6-1 |
| ITF M25 Varnamo | 2023/05/08 08:15 | Samuel Rovai v Drew Van Orderlain | 2-6,1-6 |
| ITF M25 Nottingham Qual | 2023/04/30 11:35 | Drew Van Orderlain v James Davis | 3-6,2-6 |
| ITF M25 Nottingham Qual | 2023/04/24 09:00 | Drew Van Orderlain v Michael Shaw | 2-6,1-6 |
| ITF M25 Nottingham | 2023/04/16 08:55 | Drew Van Orderlain v Ioannis Xilas | 3-6,3-6 |
| ITF M25 Montreal | 2023/03/13 19:35 | Jonathan Sorbo v Drew Van Orderlain | 6-4,6-2 |