Stadium: Court 5 Round: 25 Ground: Hardcourt indoor
| ITF M15 Norman | 2023/10/24 15:00 | Alessio Basile v Montsi, Siphosothando | 6-2,3-6,10-6 |
| ITF M15 Norman | 2023/10/23 17:30 | Vos, Matthew v Montsi, Siphosothando | 3-6,2-6 |
| ITF M25 Kigali | 2023/09/14 07:30 | S D Prajwal Dev v Montsi, Siphosothando | 6-0,6-3 |
| ITF M25 Kigali | 2023/09/13 08:35 | Montsi, Siphosothando v Tushar Madan | 6-4,6-3 |
| ITF M25 Kigali Qual | 2023/09/11 10:00 | Montsi, Siphosothando v Cheruiyot, Kevin | 6-1,6-3 |
| ITF M25 Kigali Qual | 2023/09/10 09:45 | Yash Yadav v Montsi, Siphosothando | 3-6,3-6 |
| ITF M25 Kigali | 2023/09/03 09:55 | Sharma, Atharva v Montsi, Siphosothando | 6-2,6-4 |
| ITF M25 Decatur | 2022/08/04 00:50 | Montsi, Siphosothando v Emmett Ward | 7-5,3-6,3-6 |
| ITF M15 Las Vegas | 2023/10/18 22:30 | Kaylan Bigun v Ryan Dickerson | 6-7,7-6,3-6 |
| ITF M15 Ithaca | 2023/10/03 16:30 | Kaylan Bigun v Matt Kuhar | 3-6,6-4,6-7 |
| ITF - M15 Orange Park | 2023/05/03 13:45 | Kaylan Bigun v Rehman, Huzaifa A. | 6-1,6-7,2-6 |
| ITF - M15 Vero Beach | 2023/04/26 19:40 | Gabi Adrian Boitan v Kaylan Bigun | 7-6,6-1 |
| Challenger - Tallahassee | 2023/04/17 14:00 | Kaylan Bigun v Harrison, Ryan | 2-6,6-7 |
| ITF - M15 Sunrise | 2023/04/13 15:00 | Kaylan Bigun v Kyle Kang | 5-7,4-6 |
| ITF - M15 Sunrise | 2023/04/11 21:00 | Jesse Flores v Kaylan Bigun | 1-6,4-6 |
| ITF M15 Naples | 2023/02/28 16:30 | Jonathan Mridha v Kaylan Bigun | 6-2,6-0 |