Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| ITF M15 Fayetteville | 2020/11/03 20:50 | Sam Riffice v Roberto Quiroz | 2-6,6-7 |
| UTR Pro Tennis Series Florida | 2020/07/30 12:00 | Cleeve Harper v Sam Riffice | 2-6,4-6 |
| UTR Pro Tennis Series Florida | 2020/07/29 12:00 | Sam Riffice v Egor Gerasimov | 3-6,4-6 |
| UTR Pro Tennis Series Florida | 2020/07/28 12:00 | Jordi Arconada v Sam Riffice | 3-6,3-6 |
| UTR Pro Tennis Series Florida | 2020/07/24 13:30 | Sam Riffice v Liam Draxl | 3-6,6-7 |
| UTR Pro Tennis Series Florida | 2020/07/23 12:00 | Sam Riffice v Ronald Hohmann | 6-3,6-3 |
| UTR Pro Tennis Series Florida | 2020/07/22 13:30 | Dmitry Popko v Sam Riffice | 6-4,1-6,10-8 |
| Matchplay 120 | 2020/07/21 20:00 | Shintaro Mochizuki v Sam Riffice | 3-6,6-3,0-0 |
| Challenger Cary | 2020/11/15 17:00 | Prajnesh Gunneswaran v Denis Kudla | 6-3,3-6,0-6 |
| Challenger Cary | 2020/11/13 18:20 | Prajnesh Gunneswaran v Thomaz Bellucci | 3-6,7-5,7-6 |
| Challenger Cary | 2020/11/12 17:35 | Prajnesh Gunneswaran v Jack Sock | 6-7,6-2,7-6 |
| Challenger Cary | 2020/11/10 15:30 | Prajnesh Gunneswaran v Peter Polansky | 6-2,6-2 |
| Challenger Hamburg | 2020/10/27 13:05 | Prajnesh Gunneswaran v Tobias Kamke | 6-3,4-6,1-6 |
| Challenger Ismaning | 2020/10/24 13:50 | Prajnesh Gunneswaran v Botic Van De Zandschulp | 6-7,1-6 |
| Challenger Ismaning | 2020/10/23 14:25 | Prajnesh Gunneswaran v Daniel Masur | 7-5,6-7,6-3 |
| Challenger Ismaning | 2020/10/21 18:50 | Prajnesh Gunneswaran v Lukas Lacko | 6-4,5-7,6-4 |