| UTR Pro Tennis Series Mülheim | 2021/10/15 10:00 | Sidane Pontjodikromo v Benjamin Hassan | 6-3,6-3 |
| UTR Pro Tennis Series Mülheim | 2021/10/14 10:00 | Jose Antonio Rodriguez Rodriguez v Benjamin Hassan | 4-6,1-6 |
| UTR Pro Tennis Series Mülheim | 2021/10/12 10:00 | Melchior Delloye v Benjamin Hassan | 1-6,2-5 |
| Challenger de Barcelona | 2021/10/03 11:45 | Bekkhan Atlangeriev v Benjamin Hassan | 6-2,3-6,6-1 |
| Challenger de Lisboa | 2021/09/30 09:30 | Dmitry Popko v Benjamin Hassan | 6-2,6-4 |
| Challenger de Lisboa | 2021/09/28 17:50 | Andrea Arnaboldi v Benjamin Hassan | 2-6,6-3,6-7 |
| Challenger de Lisboa | 2021/09/27 11:50 | Bogdan Bobrov v Benjamin Hassan | 3-6,1-6 |
| Challenger de Lisboa | 2021/09/26 14:20 | Henrique Rocha v Benjamin Hassan | 4-6,2-6 |
| UTR Pro Tennis Series Mülheim | 2021/10/15 07:00 | Tom Gentzsch v Christian Hansen | 4-6,1-6 |
| UTR Pro Tennis Series Mülheim | 2021/10/14 08:30 | Tom Gentzsch v Alen Moritz Hodzic | 4-6,6-2,5-4 |
| UTR Pro Tennis Series Mülheim | 2021/10/13 11:30 | Quin Verstegen v Tom Gentzsch | 4-6,2-6 |
| UTR Pro Tennis Series Mülheim | 2021/10/12 11:30 | Filip Duda v Tom Gentzsch | 6-4,5-2 |
| ITF M25 Eupen | 2021/09/07 10:05 | Guy Den Heijer v Tom Gentzsch | 6-3,6-4 |
| ITF M25 Eupen | 2021/09/06 13:30 | Nico Hornitschek v Tom Gentzsch | 4-6,4-6 |
| ITF M25 Eupen | 2021/09/05 07:30 | Tom Gentzsch v Olivier Rojas | 6-3,7-5 |
| ITF M25 Trier | 2021/08/25 09:00 | Tom Gentzsch v Ryan Nijboer | 3-6,4-6 |