| Challenger Chicago | 08/08 20:30 | 14 | [461] Gage Brymer v Tennys Sandgren [342] | 4-6,4-6 | |
| Challenger Lexington | 08/02 18:40 | 25 | [194] Gijs Brouwer v Gage Brymer [461] | 6-4,6-1 | |
| Challenger Lexington | 08/01 14:00 | 19 | Gage Brymer v Osgar O'Hoisin | 7-6,6-4 | |
| Challenger Lexington | 07/31 15:50 | 14 | [468] Gage Brymer v Divij Sharan [186] | 6-3,5-7,7-6 | |
| Challenger Indianapolis | 07/18 14:00 | 19 | [468] Gage Brymer v Hady Habib [356] | 6-7,5-7 | |
| Challenger Indianapolis | 07/17 14:00 | 14 | [353] Keegan Smith v Gage Brymer [489] | 4-6,4-6 | |
| ATP Newport | 07/11 16:25 | 19 | [146] Mitchell Krueger v Gage Brymer [489] | 6-1,6-4 | |
| ATP Newport | 07/10 20:05 | 14 | [491] Gage Brymer v Tung-Lin Wu [190] | 2-6,6-3,7-6 | |
| ITF M15 Fountain Valley | 07/07 17:00 | 26 | Gage Brymer v Yuta Kikuchi | 3-6,6-1,1-6 | |
| ITF M15 Fountain Valley | 07/06 18:15 | 25 | Gage Brymer v Michael Shabaz | 6-2,5-7,7-6 | |
| ITF M15 Los Angeles | 07/02 20:10 | 28 | [336] Brandon Holt v Gage Brymer [491] | 6-2,6-4 | |
| ITF M15 Los Angeles | 07/01 20:05 | 27 | Gage Brymer v Kyle Kang | Retired |