Stadium: Palasport Round: 45 Ground: Hardcourt indoor
| Challenger Bratislava | 2018/11/04 09:00 | Aldin Setkic v Simon, Tobias | 7-6,6-4 |
| Challenger Bratislava | 2018/11/03 08:30 | Simon, Tobias v Marcora, Roberto | 6-3,6-4 |
| Challenger Eckental | 2018/10/28 10:00 | Igor Sijsling v Simon, Tobias | 3-6,7-6,6-2 |
| Challenger Eckental | 2018/10/27 08:45 | Simon, Tobias v Aldin Setkic | 3-6,7-6,7-5 |
| Brest, France | 2018/10/21 13:45 | Brkic, Tomislav v Simon, Tobias | 6-2,6-0 |
| Brest, France | 2018/10/20 13:05 | Arthur Rinderknech v Simon, Tobias | 6-7,7-6,3-6 |
| Challenger Ismaning | 2018/10/14 12:40 | Simon, Tobias v Erler, Alexander | 6-7,6-4,6-7 |
| Challenger Ismaning | 2018/10/13 17:10 | Evan Furness v Simon, Tobias | 2-6,6-7 |
| Challenger Barletta Qual | 2018/04/07 14:25 | Lapalombella, Savino v Maxime Chazal | 0-6,1-6 |
| Challenger Andria Qual | 2017/11/18 09:00 | Lapalombella, Savino v Giuseppe Tresca | 0-6,1-6 |
| Challenger Barletta Qual | 2017/04/08 12:10 | Lapalombella, Savino v Portaluri, Giorgio | 1-6,1-6 |
| Challenger Andria Qual | 2016/11/19 13:10 | Lapalombella, Savino v Riccardo Bonadio | 0-6,1-6 |
| Challenger Barletta Qual | 2016/04/09 10:35 | Lapalombella, Savino v Lorenzo Sonego | 0-6,1-6 |