Stadium: Center Court Round: 45 Ground: Hardcourt indoor
| Challenger Almaty 2 | 2018/09/29 09:20 | Khumoyun Sultanov v Tobias Simon | 7-6,6-4 |
| Challenger Orleans | 2018/09/26 09:00 | Tobias Simon v Lorenzo Sonego | 3-6,7-6,3-6 |
| Challenger Orleans | 2018/09/24 10:35 | Hugo Nys v Tobias Simon | 4-6,6-3,6-3 |
| Challenger Orleans | 2018/09/23 12:35 | Hugo Grenier v Tobias Simon | 3-6,7-6,6-7 |
| Challenger Orleans | 2018/09/22 15:15 | Tobias Simon v Tim Puetz | 6-2,4-6,7-6 |
| Challenger Istanbul | 2018/09/10 07:30 | Tim Van Rijthoven v Tobias Simon | 6-3,7-6 |
| Challenger Istanbul | 2018/09/09 09:00 | Vladimir Polyakov v Tobias Simon | 0-6,3-6 |
| Challenger Istanbul | 2018/09/08 07:00 | Isaac Stoute v Tobias Simon | 3-6,6-4,4-6 |
| ITF Italy F22 Qual | 2018/08/04 11:15 | Petro Orlando Fellin v Alessandro G Conca | 6-4,6-1 |
| ITF Italy F21 Qual | 2018/07/28 11:35 | Mirko Cutuli v Petro Orlando Fellin | 6-3,6-2 |
| Challenger Ortisei Qual | 2017/10/07 13:55 | Petro Orlando Fellin v Yann Marti | 6-7,3-6 |
| ITF Italy F25 Qual | 2017/08/06 14:00 | Nicola Vidal v Petro Orlando Fellin | 6-2,3-6,6-4 |