Stadium: Court 3 Round: 25 Ground: Hardcourt indoor
| Challenger Launceston | 2019/01/29 23:00 | Grills, Jacob v Tatsuma Ito | 2-6,4-6 |
| Challenger Launceston | 2019/01/28 23:00 | Grills, Jacob v Bega, Alessandro | 6-7,6-2,6-3 |
| Challenger - Burnie | 2019/01/22 00:25 | Grills, Jacob v Mohamed Safwat | 4-6,2-6 |
| Challenger - Burnie | 2019/01/21 02:55 | Grills, Jacob v Lopez Perez | 6-2,6-1 |
| Challenger Canberra | 2019/01/06 01:25 | Tomas Barrios Vera v Grills, Jacob | 6-3,6-3 |
| Open d'Australie Playoff Wilcard Australienne | 2018/12/09 23:00 | Grills, Jacob v Akira Santillan | 1-6,5-7,4-6 |
| Challenger Kobe | 2018/11/12 02:00 | Grills, Jacob v Tung-Lin Wu | 2-6,4-6 |
| Challenger Kobe | 2018/11/11 03:35 | Grills, Jacob v Issei Okamura | 1-6,6-4,6-3 |
| ITF M25 Oberentfelden | 2019/02/07 19:50 | Simon, Tobias v Ehrat, Sandro | 7-6,3-6,6-7 |
| ITF M25 Oberentfelden | 2019/02/05 16:00 | Simon, Tobias v Alexander Ritschard | 6-7,6-1,7-6 |
| ITF - M25 Nussloch | 2019/01/25 13:00 | Simon, Tobias v Erler, Alexander | 4-6,6-7 |
| ITF - M25 Nussloch | 2019/01/24 13:30 | Simon, Tobias v Ryan Peniston | 7-6,6-4 |
| ITF - M25 Nussloch | 2019/01/22 11:00 | Simon, Tobias v Heger, Tim | 6-3,6-4 |
| Challenger Canberra | 2019/01/07 03:00 | Hugo Grenier v Simon, Tobias | 6-4,6-7,6-4 |
| Challenger Canberra | 2019/01/06 00:10 | Evans, Thomas v Simon, Tobias | 3-6,2-6 |
| Challenger Noumea | 2018/12/31 23:00 | Simon, Tobias v Verbeek, Sem | 5-7,7-5,4-6 |