Stadium: Court 6 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Sharm El Sheikh | 2023/10/10 07:00 | Saveliy Ivanov v Tommy Czaplinski | 3-6,6-7 |
| UTR Pro Knoxville | 2023/09/01 20:31 | Tommy Czaplinski v Tomas Rodriguez | 6-7,2-5 |
| UTR Pro Knoxville | 2023/08/31 18:00 | Shunsuke Mitsui v Tommy Czaplinski | 6-4,6-2 |
| UTR Pro Knoxville | 2023/08/30 15:00 | Juan Lugo v Tommy Czaplinski | 7-5,4-6,3-6 |
| UTR Pro Knoxville | 2023/08/28 16:00 | Jibril Nettles v Tommy Czaplinski | 7-6,6-4 |
| UTR Pro Knoxville | 2023/08/27 19:03 | Tommy Czaplinski v Michael Zhu | 7-6,6-3 |
| ITF M15 Nakhon Si Thammarat | 2023/07/20 04:40 | Yuta Kawahashi v Tommy Czaplinski | 6-3,6-2 |
| ITF M15 Nakhon Si Thammarat | 2023/07/19 03:40 | Tommy Czaplinski v Krittin Koaykul | 6-4,6-2 |
| ITF M15 Buschhausen | 2023/09/16 11:40 | Jonas Forejtek v Luca Castagnola | 7-5,6-0 |
| ITF M15 Buschhausen | 2023/09/15 10:00 | Luca Castagnola v Hazem Naw | 0-6,6-3,6-4 |
| ITF M15 Buschhausen | 2023/09/14 10:00 | Luca Castagnola v Justin Engel | 6-1,6-3 |
| ITF M15 Buschhausen | 2023/09/12 11:35 | Luca Castagnola v Lukas Palovic | 6-1,6-3 |
| Challenger Genoa | 2023/09/04 08:00 | Chun Hsin Tseng v Luca Castagnola | 6-2,6-3 |
| Challenger Genoa | 2023/09/03 11:15 | Luca Castagnola v Gabriele Piraino | 6-3,5-7,6-1 |
| Challenger Como | 2023/08/27 08:00 | Luca Castagnola v Calvin Hemery | 0-6,4-6 |
| ITF M25 Lesa | 2023/08/24 14:30 | Tim Handel v Luca Castagnola | 2-6,6-3,6-4 |