Stadium: Centre Court (2) Round: 27 Ground: Carpet indoor
| Challenger Ismaning | 2018/10/14 12:40 | Simon, Tobias v Erler, Alexander | 6-7,6-4,6-7 |
| 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 |
| Challenger Andria | 2018/11/20 21:00 | Simon, Tobias v Lorenzo Sonego | 6-7,7-5,5-7 |
| Challenger Andria | 2018/11/19 11:10 | Marc-Andrea Huesler v Simon, Tobias | 3-6,7-6,3-6 |
| Challenger Andria | 2018/11/18 14:15 | Simon, Tobias v Gojo, Borna | 7-6,6-4 |
| ITF - M25 Nussloch | 2019/01/24 09:30 | Erler, Alexander v Marc-Andrea Huesler | 5-7,6-4,6-4 |
| ITF Tunisia F45 | 2018/12/19 08:00 | Erler, Alexander v Trusendi, Walter | 0-6,1-6 |
| ITF Tunisia F44 | 2018/12/11 09:00 | Stefan Palosi v Erler, Alexander | 6-1,6-4 |
| Challenger Andria | 2018/11/20 15:35 | Caruana, Liam v Erler, Alexander | 6-1,6-7,7-5 |
| Challenger Andria | 2018/11/19 11:00 | Erler, Alexander v Frigerio, Lorenzo | 4-6,1-6 |
| Challenger Andria | 2018/11/18 10:00 | Erler, Alexander v Cutuli, Domenico | 6-4,5-7,6-1 |
| ITF Egypt F25 | 2018/11/01 08:00 | Recci, Mason v Erler, Alexander | 3-6,6-4,6-4 |
| ITF Egypt F25 | 2018/10/31 10:40 | Petrenko, Anatoliy v Erler, Alexander | 0-6,6-7 |