Stadium: Duygu Aksit Oal Round: 25 Ground: Grass
| ATP Queens | 2019/06/15 11:40 | James Ward v Prajnesh Gunneswaran | 6-1,6-4 |
| French Open | 2019/05/26 13:10 | Prajnesh Gunneswaran v Hugo Dellien | 1-6,3-6,1-6 |
| ATP Munich | 2019/04/28 11:30 | Prajnesh Gunneswaran v Denis Istomin | 6-4,2-6,2-6 |
| ATP Munich | 2019/04/27 14:00 | Prajnesh Gunneswaran v Alexander Erler | 3-6,7-6,7-5 |
| Challenger Anning | 2019/04/21 06:00 | Jay Clarke v Prajnesh Gunneswaran | 6-4,6-3 |
| Challenger Anning | 2019/04/20 04:00 | Kamil Majchrzak v Prajnesh Gunneswaran | 6-7,7-6,4-6 |
| Challenger Anning | 2019/04/19 05:30 | Nikola Milojevic v Prajnesh Gunneswaran | 5-7,3-6 |
| Challenger Anning | 2019/04/18 05:50 | Adam Pavlasek v Prajnesh Gunneswaran | 5-7,3-6 |
| French Open | 2019/05/26 10:15 | Janko Tipsarevic v Grigor Dimitrov | 3-6,0-6,6-3,7-6,4-6 |
| ATP Geneva | 2019/05/21 18:40 | Janko Tipsarevic v Hugo Dellien | 6-7,3-6 |
| ATP Geneva | 2019/05/20 16:55 | Peter Gojowczyk v Janko Tipsarevic | 5-7,5-7 |
| Challenger San Luis Potosi | 2019/04/17 21:10 | Lucas Miedler v Janko Tipsarevic | 7-5,3-6,6-3 |
| Challenger San Luis Potosi | 2019/04/17 00:55 | Janko Tipsarevic v Lucas Gomez | 6-4,5-7,6-2 |
| ATP Houston | 2019/04/12 18:30 | Sam Querrey v Janko Tipsarevic | 7-6,7-6 |
| ATP Houston | 2019/04/11 17:00 | Janko Tipsarevic v Cameron Norrie | 6-3,6-4 |
| ATP Houston | 2019/04/10 00:20 | Janko Tipsarevic v Tennys Sandgren | 6-1,7-6 |