Stadium: Centre Court Round: 25 Ground: Hardcourt outdoor
| 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 Liuzhou | 2019/10/22 06:15 | Prajnesh Gunneswaran v Nicolas Barrientos | 6-2,6-1 |
| Challenger Ningbo | 2019/10/18 05:20 | Prajnesh Gunneswaran v Steven Diez | 3-6,4-6 |
| Challenger Ningbo | 2019/10/17 07:15 | Prajnesh Gunneswaran v Tsung-Hua Yang | 7-6,6-3 |
| Challenger Ningbo | 2019/10/15 06:25 | Prajnesh Gunneswaran v Max Purcell | 6-3,6-4 |
| Challenger Kaohsiung | 2019/09/19 05:45 | Enrique Lopez-Perez v Prajnesh Gunneswaran | 5-7,7-5,6-4 |
| Challenger Kaohsiung | 2019/09/17 12:15 | Shuichi Sekiguchi v Prajnesh Gunneswaran | 3-6,2-6 |
| 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 |
| Challenger Bratislava | 2019/11/05 14:50 | Yannick Maden v Oscar Otte | 6-4,2-6,6-4 |
| Challenger Eckental | 2019/10/29 14:55 | Yannick Maden v Evgeny Karlovskiy | 4-6,3-6 |
| Challenger Brest | 2019/10/22 17:40 | Hugo Grenier v Yannick Maden | 7-6,6-4 |
| ATP Antwerp | 2019/10/16 10:00 | Frances Tiafoe v Yannick Maden | 7-6,6-3 |
| ATP Antwerp | 2019/10/14 10:00 | Norbert Gombos v Yannick Maden | 1-6,6-3,4-6 |
| ATP Antwerp | 2019/10/13 11:00 | Yannick Maden v Salvatore Caruso | 6-2,6-4 |