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