Stadium: Centre Court Round: 24 Ground: Hardcourt outdoor
| Challenger Bangkok | 2019/02/14 03:00 | Henri Laaksonen v Thiemo De Bakker | 6-4,6-3 |
| Challenger Bangkok | 2019/02/12 06:55 | Zhe Li v Thiemo De Bakker | 4-6,6-4,4-6 |
| Challenger Quimper | 2019/01/29 17:55 | Thiemo De Bakker v Matthias Bachinger | 7-6,4-6,5-7 |
| Challenger Quimper | 2019/01/28 16:20 | Thiemo De Bakker v Aslan Karatsev | 4-6,7-5,6-0 |
| Challenger Rennes | 2019/01/21 19:10 | Thiemo De Bakker v Jurij Rodionov | 6-7,6-7 |
| Challenger Koblenz | 2019/01/17 17:10 | Thiemo De Bakker v Pavel Kotov | 2-6,6-7 |
| Challenger Koblenz | 2019/01/16 16:35 | Thiemo De Bakker v Benjamin Hassan | 6-1,6-4 |
| Challenger Columbus | 2019/01/09 16:00 | Thiemo De Bakker v Lucas Miedler | 3-6,3-6 |
| Challenger Bangkok | 2019/02/14 06:15 | James Duckworth v Janko Tipsarevic | 4-6,6-3,6-2 |
| Challenger Bangkok | 2019/02/13 04:50 | Janko Tipsarevic v Marc Polmans | 6-2,3-6,6-3 |
| Challenger Bangkok | 2019/02/12 04:10 | Tsung-Hua Yang v Janko Tipsarevic | 2-6,6-4,4-6 |
| Australian Open | 2019/01/14 01:35 | Grigor Dimitrov v Janko Tipsarevic | 4-6,6-3,6-1,6-4 |
| Kooyong Classic | 2019/01/08 02:35 | Jason Kubler v Janko Tipsarevic | 4-6,6-3,10-12 |
| US Open | 2017/08/30 23:05 | Diego Schwartzman v Janko Tipsarevic | 6-2,6-4,7-5 |
| US Open | 2017/08/28 19:35 | Thanasi Kokkinakis v Janko Tipsarevic | 7-6,6-3,1-6,6-7,3-6 |
| ATP Winston-Salem | 2017/08/21 19:00 | Janko Tipsarevic v Andreas Seppi | 2-6,2-6 |