Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
| 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 |
| Australian Open | 2020/01/16 06:35 | Yannick Hanfmann v Prajnesh Gunneswaran | 6-1,2-6,1-6 |
| Australian Open | 2020/01/14 09:00 | Harry Bourchier v Prajnesh Gunneswaran | 2-6,4-6 |
| Challenger Canberra | 2020/01/07 06:45 | Prajnesh Gunneswaran v Taro Daniel | 4-6,6-7 |
| Challenger Canberra | 2020/01/06 03:20 | Prajnesh Gunneswaran v Jason Kubler | 7-5,6-3 |
| Challenger Pune | 2019/11/14 10:30 | Prajnesh Gunneswaran v Tim Van Rijthoven | 6-4,5-7,3-6 |
| Challenger Pune | 2019/11/13 10:50 | Prajnesh Gunneswaran v Chandril Sood | 6-1,6-3 |
| Challenger Burnie | 2020/01/30 03:35 | Michail Pervolarakis v Yannick Maden | 6-1,6-0 |
| Challenger Burnie | 2020/01/29 05:05 | Rio Noguchi v Yannick Maden | 2-6,2-6 |
| Australian Open | 2020/01/17 02:20 | Lorenzo Giustino v Yannick Maden | 6-7,6-2,6-4 |
| Australian Open | 2020/01/15 23:00 | Maximilian Marterer v Yannick Maden | 7-6,6-7,6-7 |
| Challenger Canberra | 2020/01/08 00:50 | Soonwoo Kwon v Yannick Maden | 6-1,6-2 |
| Challenger Canberra | 2020/01/06 23:00 | Yannick Maden v Guillermo Garcia-Lopez | 7-6,6-3 |
| Challenger Helsinki | 2019/11/13 11:00 | Yannick Maden v Rayane Roumane | 4-6,7-5,1-6 |
| Challenger Bratislava | 2019/11/07 13:10 | Yannick Maden v Lloyd Harris | 6-1,3-6,3-6 |