Stadium: Court 2N Round: 54 Ground: Hardcourt outdoor
| ITF M25 Decatur | 2019/07/29 18:00 | Pickens, A.trice v Montsi, Siphosothando | 4-6,6-3,6-10 |
| ITF M25 Decatur | 2021/08/03 16:45 | Montsi, Siphosothando v Ezekiel Clark | 3-6,6-2,15-13 |
| ITF M25 Decatur | 2021/08/02 15:00 | Brymer, Gage v Montsi, Siphosothando | 6-2,2-6,7-10 |
| ITF M25 Champaign | 2021/07/29 18:45 | Peck, Joshua v Montsi, Siphosothando | 6-3,6-7,6-4 |
| ITF M25 Champaign | 2021/07/28 19:15 | Montsi, Siphosothando v Tristan Schoolkate | 6-4,6-4 |
| ITF M15 Edwardsville | 2021/07/21 18:50 | Montsi, Siphosothando v Alexander Bernard | 6-0,5-7,6-3 |
| ITF M15 Edwardsville | 2021/07/20 14:00 | Perez, Alfredo v Montsi, Siphosothando | 6-2,4-6,5-10 |
| ITF M15 Edwardsville | 2021/07/19 15:00 | Ellefsen, Nils v Montsi, Siphosothando | 2-6,2-6 |
| ITF M15 Champaign | 2021/06/24 15:00 | Pervolarakis, Michail v Montsi, Siphosothando | 4-6,6-3,6-4 |
| ITF M25 Champaign | 2022/07/18 15:00 | Dynka, Tom v Pickens, A.trice | 1-6,2-6 |
| ITF M15 South Bend | 2022/06/22 13:25 | Monday, Johannus v Pickens, A.trice | 6-3,6-2 |
| ITF M15 South Bend | 2022/06/21 12:30 | Stefan Simeunovic v Pickens, A.trice | 2-6,3-6 |
| ITF M25 East Lansing | 2022/06/06 13:30 | Dhokia, Rahul v Pickens, A.trice | 6-4,4-6,10-7 |
| UTR Pro Tennis Series New York | 2022/01/01 16:30 | Ethan Leon v Pickens, A.trice | 4-6,7-5,7-6 |
| UTR Pro Tennis Series New York | 2021/12/31 14:00 | Sun, Michael v Pickens, A.trice | 3-6,5-7 |
| UTR Pro Tennis Series New York | 2021/12/30 16:00 | Luc Fomba v Pickens, A.trice | 6-4,5-4 |
| UTR Pro Tennis Series New York | 2021/12/29 17:30 | Jordan Chrysostom v Pickens, A.trice | 3-6,2-6 |