| ITF M25 Nottingham | 04/13 12:25 | 25 | Filip Peliwo v Tobias Simon | Retired | |
| Challenger Turin | 02/28 10:20 | - | Gijs Brouwer v Tobias Simon | Walkover | |
| Challenger Turin | 02/27 10:35 | 45 | Alessandro Spadola v Tobias Simon | 5-7,3-6 | |
| ITF M25 Glasgow | 02/16 09:50 | 25 | [494] Alastair Gray v Tobias Simon [489] | 7-6,7-6 | |
| ITF M25 Shrewsbury | 02/08 15:55 | 25 | [289] Antoine Escoffier v Tobias Simon [490] | 7-6,6-3 | |
| ITF M25 Loughborough | 01/25 15:45 | 25 | Julian Cash v Tobias Simon | 7-5,6-4 | |
| ITF M25 Bath | 01/11 12:00 | 25 | Tobias Simon v Felix Gill | 4-6,4-6 | |
| Challenger Forli | 01/02 13:40 | 14 | Matteo Gigante v Tobias Simon | 7-6,6-3 | |
| Challenger Manama | 11/22 08:00 | 19 | [455] Tobias Simon v Maximilian Neuchrist [437] | 3-6,6-4,3-6 | |
| Challenger Manama | 11/21 08:00 | 14 | [454] Tobias Simon v Eric Vanshelboim [485] | 4-6,6-3,6-0 | |
| Challenger Ortisei | 11/09 10:20 | 25 | [260] Matthias Bachinger v Tobias Simon [461] | 6-3,6-7,7-6 | |
| Challenger Ortisei | 11/08 09:30 | 19 | [461] Tobias Simon v Filip Misolic [350] | 7-5,7-6 | |
| Challenger Ortisei | 11/07 09:30 | 14 | [323] Francesco Forti v Tobias Simon [469] | 4-6,6-7 | |
| Challenger Eckental | 11/02 11:05 | 25 | [219] Ruben Bemelmans v Tobias Simon [469] | 6-7,6-3,7-5 | |
| Challenger Eckental | 11/01 11:55 | 19 | [469] Tobias Simon v Peter Heller [412] | 6-2,6-4 | |
| Challenger Eckental | 10/31 11:55 | 14 | [377] Otto Virtanen v Tobias Simon [460] | 1-6,4-6 | |
| ITF M25 Sarreguemines | 10/26 11:55 | 25 | [456] Arthur Bouquier v Tobias Simon [460] | 7-5,6-4 | |
| ITF M25 Toulouse | 10/21 09:00 | 26 | Axel Garcian v Tobias Simon | 3-6,6-2,6-1 | |
| ITF M25 Toulouse | 10/19 13:55 | 25 | Dane Sweeny v Tobias Simon | 6-7,5-7 | |
| ITF M25 Prague | 10/09 08:30 | 28 | [455] Tobias Simon v David Poljak [473] | 6-7,4-6 | |
| ITF M25 Prague | 10/08 11:10 | 27 | [455] Tobias Simon v Uladzimir Ignatik [365] | 2-6,7-6,6-4 | |
| ITF M25 Prague | 10/07 14:05 | 26 | Tobias Simon v Milos Karol | 6-4,4-6,7-6 | |
| ITF M25 Prague | 10/06 12:20 | 25 | Tobias Simon v Matthew William Donald | 6-3,4-6,6-3 | |
| ITF M25 Falun | 09/28 13:15 | 25 | Tobias Simon v Daniel Little | 6-7,3-6 | |
| Challenger Biel | 09/20 09:00 | 19 | [446] Tobias Simon v Jakub Paul [284] | 4-6,4-6 | |
| Challenger Biel | 09/19 11:15 | 14 | [483] Laurent Lokoli v Tobias Simon [432] | 4-6,2-6 | |
| Challenger Biel | 09/19 10:40 | 14 | Mischa Zverev v Tobias Simon | Cancelled | |
| ITF M25 Plaisir | 09/15 14:05 | 25 | Jurgen Briand v Tobias Simon | 6-4,7-6 | |
| Challenger Tulln | 09/06 10:25 | 19 | [377] Uladzimir Ignatik v Tobias Simon [448] | 6-4,4-6,7-5 | |
| Challenger Tulln | 09/05 13:00 | 14 | [78] Rafael Matos v Tobias Simon [448] | 6-7,2-6 |