| ITF M15 Norman | 10/25 16:30 | 25 | Siphosothando Montsi v Kaylan Bigun | 6-7,6-3,4-6 | |
| ITF M15 Norman | 10/24 15:00 | 54 | Alessio Basile v Siphosothando Montsi | 6-2,3-6,10-6 | |
| ITF M15 Norman | 10/23 17:30 | 54 | Matthew Vos v Siphosothando Montsi | 3-6,2-6 | |
| ITF M25 Kigali | 09/14 07:30 | 26 | S D Prajwal Dev v Siphosothando Montsi | 6-0,6-3 | |
| ITF M25 Kigali | 09/13 08:35 | 25 | Siphosothando Montsi v Tushar Madan | 6-4,6-3 | |
| ITF M25 Kigali - Clasificación | 09/11 10:00 | 54 | Siphosothando Montsi v Kevin Cheruiyot | 6-1,6-3 | |
| ITF M25 Kigali - Clasificación | 09/10 09:45 | 54 | Yash Yadav v Siphosothando Montsi | 3-6,3-6 | |
| ITF M25 Kigali | 09/03 09:55 | 54 | Atharva Sharma v Siphosothando Montsi | 6-2,6-4 | |
| ITF M25 Decatur | 08/04 00:50 | 25 | Siphosothando Montsi v Emmett Ward | 7-5,3-6,3-6 | |
| ITF M25 Decatur | 08/02 23:15 | 54 | Siphosothando Montsi v Presley Thieneman | 6-1,6-2 | |
| ITF M25 Champaign | 07/20 14:00 | 25 | Siphosothando Montsi v Cannon Kingsley | 5-7,1-6 | |
| ITF M25 Champaign | 07/19 15:00 | 54 | Siphosothando Montsi v A.Trice Pickens | 6-2,6-7,10-8 | |
| ITF M25 Decatur | 08/04 17:25 | 25 | Siphosothando Montsi v Alex Rybakov | Cancelled | |
| ITF M25 Decatur | 08/03 16:45 | 54 | Siphosothando Montsi v Ezekiel Clark | 3-6,6-2,15-13 | |
| ITF M25 Decatur | 08/02 15:00 | 54 | Gage Brymer v Siphosothando Montsi | 6-2,2-6,7-10 | |
| ITF M25 Champaign | 07/29 18:45 | 26 | Joshua Peck v Siphosothando Montsi | 6-3,6-7,6-4 | |
| ITF M25 Champaign | 07/28 19:15 | 25 | Siphosothando Montsi v Tristan Schoolkate | 6-4,6-4 | |
| ITF M15 Edwardsville | 07/22 16:15 | 26 | Paul Jubb v Siphosothando Montsi | Retired | |
| ITF M15 Edwardsville | 07/21 18:50 | 25 | Siphosothando Montsi v Alexander Bernard | 6-0,5-7,6-3 | |
| ITF M15 Edwardsville | 07/20 14:00 | 54 | Alfredo Perez v Siphosothando Montsi | 6-2,4-6,5-10 | |
| ITF M15 Edwardsville | 07/19 15:00 | 54 | Nils Ellefsen v Siphosothando Montsi | 2-6,2-6 | |
| ITF M15 Champaign | 06/24 15:00 | 26 | Michail Pervolarakis v Siphosothando Montsi | 4-6,6-3,6-4 | |
| ITF M15 Champaign | 06/23 17:10 | 25 | Siphosothando Montsi v Victor Lilov | 6-4,6-1 | |
| ITF M15 Champaign | 09/10 18:00 | 25 | Nick Chappell v Siphosothando Montsi | 7-5,6-2 | |
| ITF M25 Decatur | 07/30 16:40 | 54 | Gui Gomes v Siphosothando Montsi | 7-6,1-6,10-8 | |
| ITF M25 Decatur | 07/29 18:00 | 54 | A.Trice Pickens v Siphosothando Montsi | 4-6,6-3,6-10 | |
| ITF M25 Champaign | 07/25 23:00 | 26 | Axel Geller v Siphosothando Montsi | 6-4,6-2 | |
| ITF M25 Champaign | 07/23 21:25 | 25 | Siphosothando Montsi v Aziz Dougaz | 6-4,6-3 | |
| ITF M15 Champaign | 06/05 18:15 | 25 | Gui Gomes v Siphosothando Montsi | 3-6,6-2,7-6 | |
| ITF M25 Tucson | 01/09 21:15 | 25 | Siphosothando Montsi v Lloyd Glasspool | 4-6,6-3,3-6 |