Stadium: Stadium 17 Round: 15 Ground: Hardcourt outdoor
| Challenger Rome | 2022/04/26 12:45 | Gian Marco Moroni v Gilles Simon | 6-1,6-4 |
| ATP Belgrade | 2022/04/17 13:10 | Gilles Simon v Damir Dzumhur | 6-3,5-7,2-6 |
| Challenger Barletta | 2022/04/12 12:10 | Gilles Simon v Marius Copil | 2-6,6-4,4-6 |
| Challenger St Brieuc | 2022/03/30 17:35 | Gilles Simon v Evgeny Karlovskiy | 7-6,6-7,5-7 |
| ATP Miami | 2022/03/23 16:20 | Gilles Simon v Jack Draper | 5-7,1-6 |
| Challenger Phoenix | 2022/03/16 17:00 | Gilles Simon v Christopher Eubanks | 4-6,5-7 |
| Challenger Phoenix | 2022/03/15 18:25 | Gilles Simon v Tomas Machac | 7-5,6-1 |
| Challenger Phoenix | 2022/03/14 20:45 | Gilles Simon v Murphy Cassone | 6-3,6-1 |
| Challenger Rome | 2022/04/27 13:00 | Jesper De Jong v Matteo Arnaldi | 6-1,3-6,6-3 |
| Challenger Rome | 2022/04/26 11:00 | Matteo Arnaldi v Nikola Milojevic | 2-6,6-4,6-0 |
| Challenger Split | 2022/04/23 13:40 | Matteo Arnaldi v Christopher O'Connell | 5-7,2-6 |
| Challenger Split | 2022/04/23 07:30 | Matteo Arnaldi v Andrea Arnaboldi | 6-7,7-6,6-2 |
| Challenger Split | 2022/04/21 10:30 | Duje Ajdukovic v Matteo Arnaldi | 7-5,4-6,4-6 |
| Challenger Split | 2022/04/19 12:40 | Michael Geerts v Matteo Arnaldi | 3-6,4-6 |
| Challenger Split | 2022/04/18 08:30 | Daniel Michalski v Matteo Arnaldi | 1-6,2-6 |
| Challenger Split | 2022/04/17 10:15 | Arjun Kadhe v Matteo Arnaldi | 3-6,0-6 |