Stadium: Center Court Round: 24 Ground: Clay
| Challenger Mallorca | 2018/08/29 12:25 | Roberto Ortega-Olmedo v Kenny de Schepper | 6-7,4-6 |
| Challenger Segovia | 2016/07/27 16:00 | Kenny de Schepper v Roberto Ortega-Olmedo | 6-3,6-3 |
| Challenger Cherbourg | 2019/02/11 10:00 | Roberto Ortega-Olmedo v Zdenek Kolar | 1-6,2-6 |
| Challenger Quimper | 2019/01/28 10:50 | Mathias Bourgue v Roberto Ortega-Olmedo | 4-6,7-6,6-4 |
| Challenger Koblenz | 2019/01/20 13:00 | Gianluca Mager v Roberto Ortega-Olmedo | 2-6,7-6,6-2 |
| Challenger Koblenz | 2019/01/19 16:00 | Pavel Kotov v Roberto Ortega-Olmedo | 5-7,6-3,3-6 |
| Challenger Koblenz | 2019/01/18 17:25 | Mikael Ymer v Roberto Ortega-Olmedo | 7-6,1-6,3-6 |
| Challenger Koblenz | 2019/01/17 18:15 | Roberto Ortega-Olmedo v Yannick Maden | 6-4,3-6,6-3 |
| Challenger Koblenz | 2019/01/15 18:50 | Zdenek Kolar v Roberto Ortega-Olmedo | 2-6,4-6 |
| Challenger Koblenz | 2019/01/14 18:20 | Marek Gengel v Roberto Ortega-Olmedo | 6-7,3-6 |
| ATP Montpellier | 2019/02/03 13:10 | Kenny de Schepper v Quentin Halys | 4-6,6-3,0-6 |
| Challenger Koblenz | 2019/01/17 15:30 | Carlos Taberner v Kenny de Schepper | 7-6,6-2 |
| Challenger Koblenz | 2019/01/15 10:35 | Jose Hernandez-Fernandez v Kenny de Schepper | 2-6,1-6 |
| Australian Open | 2019/01/07 23:00 | Kenny de Schepper v Sergiy Stakhovsky | 3-6,6-4,3-6 |
| Challenger Noumea | 2019/01/02 02:45 | Gleb Sakharov v Kenny de Schepper | 7-6,6-4 |
| Czechia Extraliga | 2018/12/15 13:32 | Szymon Walkow v Kenny de Schepper | 2-6,1-5 |
| Czechia Extraliga | 2018/12/14 09:00 | Kenny de Schepper v Michael Vrbensky | 6-1,6-4 |
| Challenger Mouilleron le Captif | 2018/11/07 18:15 | Benoit Paire v Kenny de Schepper | 6-4,7-6 |