Stadium: Court 6 Round: 54 Ground: Hardcourt indoor
| ITF M25 Columbus | 2023/11/16 16:00 | Radu Mihai Papoe v Preston Stearns | 6-1,6-1 |
| ITF M25 Columbus | 2023/11/15 15:55 | Patrick Maloney v Preston Stearns | 6-1,4-6,2-6 |
| 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 |
| ITF M15 Heraklion | 2023/11/22 13:05 | Jannik Maute v Simon Freund | 6-3,6-3 |
| ITF M15 Heraklion | 2023/11/21 07:00 | Lars Goran Verwerft v Simon Freund | 6-1,5-7,8-10 |
| ITF M15 Heraklion | 2023/11/20 13:45 | Adrian Arcon v Simon Freund | 2-6,0-6 |
| ITF M15 Heraklion | 2023/11/19 15:30 | Vincent Jonah Strauch v Simon Freund | 3-6,3-6 |
| ITF M25 Heraklion | 2023/11/14 07:30 | James Davis v Simon Freund | 6-4,5-7,10-7 |
| ITF M25 Heraklion | 2023/11/13 08:30 | Graham Maassen v Simon Freund | 3-6,2-6 |
| ITF M25 Heraklion | 2023/11/07 07:30 | Guy Den Heijer v Simon Freund | 6-2,3-6,10-5 |
| ITF M25 Heraklion | 2023/11/06 07:00 | Graham Maassen v Simon Freund | 4-6,2-6 |