Stadium: Court 1 Round: 54 Ground: Hardcourt outdoor
| ITF M25 Champaign | 2021/07/28 17:35 | Brymer, Gage v Rio Noguchi | 6-7,2-6 |
| ATP - Los Cabos | 2021/07/18 02:40 | Brymer, Gage v Alex Rybakov | 3-6,4-6 |
| ITF M15 Champaign | 2021/06/26 15:00 | Jason Kubler v Brymer, Gage | 6-0,6-3 |
| ITF M15 Champaign | 2021/06/25 16:55 | Kenyatte, Kweisi v Brymer, Gage | 2-6,4-6 |
| ITF M15 Champaign | 2021/06/24 20:25 | Dane Sweeny v Brymer, Gage | 6-7,6-7 |
| ITF M15 Champaign | 2021/06/23 16:50 | Brymer, Gage v Sho Shimabukuro | 3-6,6-2,6-1 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2021/06/18 14:00 | Brymer, Gage v Riffice, Sam | 0-6,6-7 |
| Tulsa, Singles Main, M-ITF-USA-16A | 2021/06/17 13:55 | Gonzalo Villanueva v Brymer, Gage | 4-6,3-6 |
| 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 M15 Champaign | 2021/06/23 17:10 | Montsi, Siphosothando v Victor Lilov | 6-4,6-1 |
| ITF M15 Champaign | 2019/09/10 18:00 | Nick Chappell v Montsi, Siphosothando | 7-5,6-2 |