Stadium: Center Court Round: 54 Ground: Clay
| ITF M25 Kigali Qual | 2023/09/10 09:45 | Yash Yadav v Siphosothando Montsi | 3-6,3-6 |
| ITF M25 Kigali | 2023/09/03 09:55 | Atharva Sharma v Siphosothando Montsi | 6-2,6-4 |
| ITF M25 Decatur | 2022/08/04 00:50 | Siphosothando Montsi v Emmett Ward | 7-5,3-6,3-6 |
| ITF M25 Decatur | 2022/08/02 23:15 | Siphosothando Montsi v Presley Thieneman | 6-1,6-2 |
| ITF M25 Champaign | 2022/07/20 14:00 | Siphosothando Montsi v Cannon Kingsley | 5-7,1-6 |
| ITF M25 Champaign | 2022/07/19 15:00 | Siphosothando Montsi v A.trice Pickens | 6-2,6-7,10-8 |
| ITF M25 Decatur | 2021/08/03 16:45 | Siphosothando Montsi v Ezekiel Clark | 3-6,6-2,15-13 |
| ITF M25 Decatur | 2021/08/02 15:00 | Gage Brymer v Siphosothando Montsi | 6-2,2-6,7-10 |
| ITF M25 Kigali Qual | 2023/09/10 11:55 | Kevin Cheruiyot v Rishiraj Shekhawat | 6-2,6-3 |
| ITF M25 Kigali | 2023/09/05 08:35 | Michael Bassem Sobhy v Kevin Cheruiyot | 6-0,6-1 |
| ITF M25 Bendigo | 2022/03/06 04:00 | Nikita Volonski v Kevin Cheruiyot | 6-0,6-1 |
| ITF M15 Sharm El Sheikh | 2020/02/23 09:00 | Alec Beckley v Kevin Cheruiyot | 6-1,6-3 |
| ITF M15 Sharm El Sheikh | 2020/02/17 08:00 | Kevin Cheruiyot v Oleksandr Ovcharenko | 4-6,1-6 |
| ITF M15 Sharm El Sheikh | 2020/02/16 08:00 | Kevin Cheruiyot v Muzingaye D. A. Sibanda | 7-6,6-2 |
| ITF M15 Sharm El Sheikh | 2020/02/09 09:00 | Amr Asrawy v Kevin Cheruiyot | 6-1,6-2 |
| ITF M15 Maputo | 2019/11/13 13:05 | Kevin Cheruiyot v Eric Vanshelboim | 1-6,5-7 |