Stadium: Indoor 5 Round: 26 Ground: Hardcourt outdoor
| 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 Bengaluru | 2020/02/12 05:30 | Prajnesh Gunneswaran v Sebastian Fanselow | 6-2,4-6,6-4 |
| ATP Pune | 2020/02/06 13:10 | Soonwoo Kwon v Prajnesh Gunneswaran | 6-3,7-6 |
| ATP Pune | 2020/02/04 13:10 | Prajnesh Gunneswaran v Yannick Maden | 7-6,7-6 |
| Australian Open | 2020/01/20 23:30 | Tatsuma Ito v Prajnesh Gunneswaran | 6-4,6-2,7-5 |
| Australian Open | 2020/01/17 05:05 | Ernests Gulbis v Prajnesh Gunneswaran | 7-6,6-2 |
| US Open | 2020/09/02 18:10 | Adrian Mannarino v Jack Sock | 7-6,7-5,6-2 |
| US Open | 2020/08/31 17:40 | Jack Sock v Pablo Cuevas | 3-6,6-4,6-2,4-6,7-6 |
| Challenger Indian Wells | 2020/03/08 19:40 | Jack Sock v Steve Johnson | 4-6,4-6 |
| Challenger Indian Wells | 2020/03/07 22:00 | Jack Sock v Brandon Nakashima | 6-7,6-3,6-4 |
| Challenger Indian Wells | 2020/03/06 19:35 | Jack Sock v Denis Kudla | 7-6,5-7,6-4 |
| Challenger Indian Wells | 2020/03/05 18:00 | Jack Sock v Evgeny Donskoy | 6-4,4-6,7-6 |
| Challenger Indian Wells | 2020/03/03 21:40 | Ugo Humbert v Jack Sock | 6-7,4-6 |
| Challenger Indian Wells | 2020/03/02 20:50 | Kaichi Uchida v Jack Sock | 1-6,7-5,2-6 |