Stadium: Court 2N Round: 54 Ground: Hardcourt outdoor
| ITF M25 Decatur | 2019/07/29 18:00 | A.Trice Pickens v Siphosothando Montsi | 4-6,6-3,6-10 |
| 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 Champaign | 2021/07/29 18:45 | Joshua Peck v Siphosothando Montsi | 6-3,6-7,6-4 |
| ITF M25 Champaign | 2021/07/28 19:15 | Siphosothando Montsi v Tristan Schoolkate | 6-4,6-4 |
| ITF M15 Edwardsville | 2021/07/21 18:50 | Siphosothando Montsi v Alexander Bernard | 6-0,5-7,6-3 |
| ITF M15 Edwardsville | 2021/07/20 14:00 | Alfredo Perez v Siphosothando Montsi | 6-2,4-6,5-10 |
| ITF M15 Edwardsville | 2021/07/19 15:00 | Nils Ellefsen v Siphosothando Montsi | 2-6,2-6 |
| ITF M15 Champaign | 2021/06/24 15:00 | Michail Pervolarakis v Siphosothando Montsi | 4-6,6-3,6-4 |
| ITF M25 Champaign | 2022/07/18 15:00 | Tom Dynka v A.Trice Pickens | 1-6,2-6 |
| ITF M15 South Bend | 2022/06/22 13:25 | Johannus Monday v A.Trice Pickens | 6-3,6-2 |
| ITF M15 South Bend | 2022/06/21 12:30 | Stefan Simeunovic v A.Trice Pickens | 2-6,3-6 |
| ITF M25 East Lansing | 2022/06/06 13:30 | Rahul Dhokia v A.Trice Pickens | 6-4,4-6,10-7 |
| UTR Pro Tennis Series New York | 2022/01/01 16:30 | Ethan Leon v A.Trice Pickens | 4-6,7-5,7-6 |
| UTR Pro Tennis Series New York | 2021/12/31 14:00 | Michael Sun v A.Trice Pickens | 3-6,5-7 |
| UTR Pro Tennis Series New York | 2021/12/30 16:00 | Luc Fomba v A.Trice Pickens | 6-4,5-4 |
| UTR Pro Tennis Series New York | 2021/12/29 17:30 | Jordan Chrysostom v A.Trice Pickens | 3-6,2-6 |