Stadium: Court 6 Round: 54 Ground: Hardcourt indoor
| Challenger Columbus | 2023/09/18 19:25 | Aidan Mayo v Preston Stearns | 6-4,6-1 |
| Challenger Columbus | 2023/09/17 19:10 | Preston Stearns v Nathan Ponwith | 6-7,6-4,6-3 |
| 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 |
| ITF M25 Falun | 2023/09/25 07:55 | Jonas Trinker v Simon Freund | 5-7,6-1,10-2 |
| ITF M25 Falun | 2023/09/24 10:00 | Fabian Hansch Mauritzson v Simon Freund | 1-6,6-7 |
| ITF M15 Danderyd | 2023/09/20 09:55 | Simon Freund v Tibo Colson | 3-6,4-6 |
| ITF M15 Danderyd | 2023/09/19 08:00 | Simon Freund v Drew Van Orderlain | 6-4,6-3 |
| 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 |