Stadium: Court 6 Round: 54 Ground: Hardcourt indoor
| ITF M15 Pittsburgh | 2023/07/24 14:00 | Emmett Ward v Preston Stearns | 6-2,6-1 |
| UTR Pro Florida | 2023/07/09 13:05 | Matthew Rankin v Preston Stearns | 7-6,6-3 |
| UTR Pro Florida | 2023/07/07 16:48 | Kabeer Kapasi v Preston Stearns | 2-6,2-6 |
| UTR Pro Florida | 2023/07/05 18:42 | Preston Stearns v Jean-Christian Morandais | 7-6,6-3 |
| UTR Pro Florida | 2023/07/04 17:40 | Preston Stearns v Jordan Chrysostom | 6-2,6-4 |
| UTR Pro Florida | 2023/07/03 12:00 | Preston Stearns v Jerry Barton | 6-7,1-6 |
| UTR Pro Charleston | 2023/06/11 13:00 | Preston Stearns v Jelani Sarr | 1-6,2-6 |
| UTR Pro Charleston | 2023/06/08 19:00 | Preston Stearns v Francisco Bastias | 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 Monastir | 2023/02/22 12:35 | Simon Freund v Niccolo Baroni | 7-5,4-6,2-6 |