Stadium: Center Court Round: 25 Ground: Clay
| Challenger Biella | 2020/09/28 10:00 | Maxime Cressy v Prajnesh Gunneswaran | 7-6,6-4 |
| French Open | 2020/09/23 12:55 | Aleksandar Vukic v Prajnesh Gunneswaran | 6-4,7-6 |
| French Open | 2020/09/21 10:10 | Cem Ilkel v Prajnesh Gunneswaran | 3-6,1-6 |
| ATP Kitzbuhel | 2020/09/08 10:00 | Marc-Andrea Huesler v Prajnesh Gunneswaran | 6-3,6-3 |
| ATP Kitzbuhel | 2020/09/07 12:50 | Sandro Kopp v Prajnesh Gunneswaran | 4-6,6-1,4-6 |
| Davis Cup | 2020/03/06 14:00 | Borna Gojo v Prajnesh Gunneswaran | 3-6,6-4,6-2 |
| ATP Dubai | 2020/02/25 10:00 | Prajnesh Gunneswaran v Dennis Novak | 4-6,3-6 |
| Challenger Bengaluru | 2020/02/13 10:55 | Prajnesh Gunneswaran v Benjamin Bonzi | 6-7,0-6 |
| Challenger Biella | 2020/09/29 13:05 | Paolo Lorenzi v Stefano Napolitano | 4-6,3-6 |
| French Open | 2020/09/21 08:00 | Botic Van De Zandschulp v Paolo Lorenzi | 7-6,6-3 |
| ATP Rome | 2020/09/12 18:25 | Paolo Lorenzi v Federico Coria | 6-3,4-6,5-7 |
| US Open | 2020/08/31 18:10 | Paolo Lorenzi v Brandon Nakashima | 3-6,2-6,6-7 |
| Battle of Bradenton | 2020/07/04 16:30 | Paolo Lorenzi v Shintaro Mochizuki | 6-4,6-0 |
| Battle of Bradenton | 2020/07/03 14:00 | Vasil Kirkov v Paolo Lorenzi | 4-6,4-6 |
| Battle of Bradenton | 2020/07/02 14:00 | Sebastian Korda v Paolo Lorenzi | 6-7,6-3,8-10 |
| Battle of Bradenton | 2020/06/19 14:00 | Axel Geller v Paolo Lorenzi | 6-1,6-4 |