| Challenger Andria | 11/19 11:10 | 54 | [392] Marc-Andrea Huesler v Simon, Tobias [466] | 3-6,7-6,3-6 | |
| Challenger Andria | 11/18 14:15 | 46 | [466] Simon, Tobias v Gojo, Borna [410] | 7-6,6-4 | |
| Challenger Andria | 11/17 12:10 | 45 | Simon, Tobias v Lapalombella, Savino | 6-0,6-1 | |
| Challenger Bratislava | 11/04 09:00 | 46 | [342] Aldin Setkic v Simon, Tobias [462] | 7-6,6-4 | |
| Challenger Bratislava | 11/03 08:30 | 45 | [462] Simon, Tobias v Marcora, Roberto [296] | 6-3,6-4 | |
| Challenger Eckental | 10/28 10:00 | 46 | [448] Igor Sijsling v Simon, Tobias [466] | 3-6,7-6,6-2 | |
| Challenger Eckental | 10/27 08:45 | 45 | [466] Simon, Tobias v Aldin Setkic [340] | 3-6,7-6,7-5 | |
| Brest, France | 10/21 13:45 | 46 | [269] Brkic, Tomislav v Simon, Tobias [427] | 6-2,6-0 | |
| Brest, France | 10/20 13:05 | 45 | [404] Arthur Rinderknech v Simon, Tobias [427] | 6-7,7-6,3-6 | |
| Challenger Ismaning | 10/14 12:40 | 46 | [433] Simon, Tobias v Erler, Alexander [426] | 6-7,6-4,6-7 | |
| Challenger Ismaning | 10/13 17:10 | 45 | Evan Furness v Simon, Tobias | 2-6,6-7 | |
| Challenger Ortisei | 10/09 08:30 | 25 | [433] Simon, Tobias v Ricardas Berankis [107] | 6-7,4-6 | |
| Challenger Ortisei | 10/08 08:00 | 54 | [433] Simon, Tobias v Aldin Setkic [313] | 7-6,6-7,7-6 | |
| Challenger Ortisei | 10/07 08:00 | 46 | [299] Heyman, Christopher v Simon, Tobias [428] | 3-6,6-7 | |
| Challenger Ortisei | 10/06 08:00 | 45 | Simon, Tobias v Fellin, Pietro Orlando | 6-2,6-1 | |
| Challenger Almaty 2 | 09/29 09:20 | 45 | Khumoyun Sultanov v Simon, Tobias | 7-6,6-4 | |
| Orleans, France | 09/26 09:00 | 25 | [432] Simon, Tobias v Lorenzo Sonego [89] | 3-6,7-6,3-6 | |
| Orleans, France | 09/24 10:35 | 54 | [80] Hugo Nys v Simon, Tobias [432] | 4-6,6-3,6-3 | |
| Orleans, France | 09/23 12:35 | 46 | [383] Hugo Grenier v Simon, Tobias [436] | 3-6,7-6,6-7 | |
| Orleans, France | 09/22 15:15 | 45 | [436] Simon, Tobias v Puetz, Tim [320] | 6-2,4-6,7-6 | |
| Istanbul, Turkey | 09/10 07:30 | 54 | [498] van Rijthoven, Tim v Simon, Tobias [426] | 6-3,7-6 | |
| Istanbul, Turkey | 09/09 09:00 | 46 | Polyakov, Vladimir v Simon, Tobias | 0-6,3-6 | |
| Istanbul, Turkey | 09/08 07:00 | 45 | Stoute, Isaac v Simon, Tobias | 3-6,6-4,4-6 | |
| Challenger Mallorca | 08/30 12:25 | 26 | [178] Bachinger, Matthias v Simon, Tobias [446] | Retired | |
| Challenger Mallorca | 08/28 09:30 | 25 | [446] Simon, Tobias v Guttierrez-Ferrol, Sergio [162] | 6-3,6-2 | |
| Challenger Mallorca | 08/27 11:10 | 54 | [446] Simon, Tobias v Hugo Grenier [362] | 7-5,2-6,7-6 | |
| Challenger Mallorca | 08/26 15:45 | 46 | Simon, Tobias v Federico Zeballos | 7-6,7-6 | |
| Challenger Mallorca | 08/26 10:45 | 45 | [349] Mertens, Yannick v Simon, Tobias [444] | 7-6,4-6,4-6 | |
| Challenger Pullach Qual | 08/04 15:25 | 45 | [456] Zizou Bergs v Simon, Tobias [474] | 6-4,7-6 | |
| ITF Italy F21 | 08/03 14:30 | 28 | [365] Souza, Joao Olavo v Simon, Tobias [474] | 7-6,7-6 |