Stadium: Court 1 Round: 27 Ground: Clay
| ITF M15 Weston | 2021/07/02 20:50 | Federico Agustin Gomez v Cannon Kingsley | 6-3,3-6,6-10 |
| ITF M15 Weston | 2021/07/01 20:06 | Alan Kohen v Cannon Kingsley | 3-6,1-6 |
| ITF M15 Weston | 2021/07/01 16:25 | Alan Kohen v Cannon Kingsley | 3-6,1-6 |
| UTR Pro Tennis Series Florida | 2020/12/19 18:00 | Cannon Kingsley v Cristian C. Rodriguez Sanchez | 6-2,4-6,3-5 |
| UTR Pro Tennis Series Florida | 2020/12/17 18:00 | JanMagnus Johnson v Cannon Kingsley | 5-7,4-6 |
| UTR Pro Tennis Series Florida | 2020/12/16 14:00 | Cannon Kingsley v Tyler Zink | 6-3,6-3 |
| UTR Pro Tennis Series Florida | 2020/12/15 16:15 | Cannon Kingsley v Garrett Johns | 5-7,6-4,7-6 |
| UTR Pro Tennis Series Florida | 2020/12/14 16:00 | Cannon Kingsley v Tristan McCormick | 7-5,6-6 |
| ITF M15 Weston | 2021/07/02 19:15 | Axel Nefve v Gonzalo Villanueva | 6-2,1-6,8-10 |
| ITF M15 Weston | 2021/07/01 21:10 | Kyle Seelig v Gonzalo Villanueva | 6-3,6-7,6-7 |
| ITF M15 Weston | 2021/07/01 15:25 | Kyle Seelig v Gonzalo Villanueva | 6-3,6-7,6-7 |
| ITF M15 Champaign | 2021/06/23 17:15 | Gonzalo Villanueva v Kweisi Kenyatte | 6-3,6-7,4-6 |
| ITF M25 Tulsa | 2021/06/17 13:55 | Gonzalo Villanueva v Gage Brymer | 4-6,3-6 |
| ITF M25 Tulsa | 2021/06/16 16:30 | Adrian Andreev v Gonzalo Villanueva | 6-2,3-6,4-6 |
| Challenger Orlando | 2021/06/06 16:10 | Adrian Andreev v Gonzalo Villanueva | 3-6,6-3,7-6 |
| Challenger Little Rock | 2021/05/30 20:10 | Zachary Svajda v Gonzalo Villanueva | 6-0,5-7,6-2 |