Stadium: Center Court Round: 19 Ground: Carpet indoor
| ITF Bahrain F1 | 2015/03/23 08:00 | Peter Heller v Tobias Simon | 7-5,6-7,3-6 |
| Challenger Eckental | 2021/10/31 11:55 | Otto Virtanen v Tobias Simon | 1-6,4-6 |
| ITF M25 Sarreguemines | 2021/10/26 11:55 | Arthur Bouquier v Tobias Simon | 7-5,6-4 |
| ITF M25 Toulouse | 2021/10/21 09:00 | Axel Garcian v Tobias Simon | 3-6,6-2,6-1 |
| ITF M25 Toulouse | 2021/10/19 13:55 | Dane Sweeny v Tobias Simon | 6-7,5-7 |
| ITF M25 Prague | 2021/10/09 08:30 | Tobias Simon v David Poljak | 6-7,4-6 |
| ITF M25 Prague | 2021/10/08 11:10 | Tobias Simon v Uladzimir Ignatik | 2-6,7-6,6-4 |
| ITF M25 Prague | 2021/10/07 14:05 | Tobias Simon v Milos Karol | 6-4,4-6,7-6 |
| ITF M25 Prague | 2021/10/06 12:20 | Tobias Simon v Matthew William Donald | 6-3,4-6,6-3 |
| ITF M15 Antalya | 2021/10/26 08:25 | Peter Heller v Jack Pinnington Jones | 3-6,4-6 |
| Challenger Lisbon | 2021/09/27 09:00 | Santiago Rodriguez Taverna v Peter Heller | 7-6,7-5 |
| Challenger Lisbon | 2021/09/26 11:25 | Luis Faria v Peter Heller | 1-6,7-6,4-6 |
| Challenger Braga | 2021/09/21 09:00 | Thiago Monteiro v Peter Heller | 6-3,6-3 |
| Challenger Braga | 2021/09/19 09:00 | Miguel Gomes v Peter Heller | 0-6,1-6 |
| ITF M15 Allershausen | 2021/09/02 13:40 | Peter Heller v Guy Den Ouden | 6-7,3-6 |
| ITF M15 Allershausen | 2021/09/01 11:15 | Peter Heller v Henri Squire | 6-3,3-6,6-4 |
| ITF M25 Caslano | 2021/08/25 10:25 | Peter Heller v Patrick Kypson | 6-3,3-6,2-6 |