Stadium: Court 3 Round: 44
| ITF M25 Portoviejo | 2021/07/26 14:30 | Gomez, Mateo v Juan Sebastian Osorio | 7-5,6-3 |
| ITF M25 Portoviejo | 2021/07/25 14:30 | Zambrano Poggi, Giuliano Franco v Juan Sebastian Osorio | 1-6,1-6 |
| ITF - M25 Santo Domingo | 2021/06/06 13:00 | Juan Sebastian Osorio v Franco Ribero | 2-6,6-3,8-10 |
| ITF - M25 Santo Domingo | 2021/05/31 13:00 | Justin Roberts v Juan Sebastian Osorio | 6-3,7-6 |
| ITF - M25 Santo Domingo | 2021/05/30 13:00 | Salazar, Amador v Juan Sebastian Osorio | 2-6,6-3,8-10 |
| Colombian National Exhibition | 2020/08/21 19:30 | Juan Sebastian Osorio v Andres Urrea | 6-7,4-6 |
| Colombian National Exhibition | 2020/08/21 14:00 | Juan Sebastian Gomez v Juan Sebastian Osorio | 0-6,6-3,3-6 |
| Colombian National Exhibition | 2020/08/20 20:30 | Felipe Rincon v Juan Sebastian Osorio | 3-6,3-6 |
| ITF M25 Portoviejo | 2021/07/26 14:30 | Mateo Barreiros Reyes v Kessler, Mcclain | 6-1,6-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/16 15:54 | Kessler, Mcclain v Phillip Jordan | 4-6,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/07/15 16:30 | Kessler, Mcclain v Thomson, Connor | 6-3,2-1 |
| UTR Pro Tennis Series Atlanta | 2021/07/13 21:00 | Kessler, Mcclain v Ravichander, Ishaan | 6-7,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/07/12 13:30 | Kessler, Mcclain v Rehman, Huzaifa A. | 6-4,5-3 |
| UTR Pro Tennis Series Atlanta | 2021/04/18 12:30 | Kessler, Mcclain v Daniel Milavsky | 6-3,4-6,4-6 |
| UTR Pro Tennis Series Atlanta | 2021/04/17 12:30 | Kessler, Mcclain v Jonny Ho | 6-2,6-6 |
| UTR Pro Tennis Series Atlanta | 2021/04/16 15:30 | Kessler, Mcclain v Haim, Matthias | 6-7,3-6 |