| Challenger de Meerbusch | 2019/08/15 11:00 | Carlos Taberner v Benjamin Hassan | 7-6,6-3 |
| Challenger de Augsburgo | 2019/08/08 09:00 | Benjamin Hassan v Facundo Mena | 6-4,1-6,0-6 |
| Challenger de Augsburgo | 2019/08/06 14:30 | Lukas Rosol v Benjamin Hassan | 4-6,4-6 |
| Challenger de Augsburgo | 2019/08/05 11:05 | Tak Khunn Wang v Benjamin Hassan | 2-6,4-6 |
| Challenger de Tampere | 2019/07/24 09:35 | Kimmer Coppejans v Benjamin Hassan | 6-3,6-3 |
| Challenger de Tampere | 2019/07/22 13:30 | Panu Virtanen v Benjamin Hassan | 6-7,1-6 |
| Challenger de Braunschweig | 2019/07/07 13:35 | Jozef Kovalik v Benjamin Hassan | 6-4,6-7,6-4 |
| Challenger de Ludwigshafen | 2019/07/04 16:00 | Benjamin Hassan v Alex Molcan | 3-6,2-6 |
| ITF M25 Trieste | 2019/09/03 11:35 | Khumoyun Sultanov v Riccardo Balzerani | 5-7,1-6 |
| Challenger de Como | 2019/08/27 08:00 | Giulio Zeppieri v Khumoyun Sultanov | 6-2,6-0 |
| Challenger de Como | 2019/08/26 08:00 | Khumoyun Sultanov v Riccardo Balzerani | 6-3,7-6 |
| Challenger de L'Aquila | 2019/08/20 10:45 | Dmitry Popko v Khumoyun Sultanov | 6-3,6-4 |
| Challenger de L'Aquila | 2019/08/19 09:30 | Khumoyun Sultanov v Lorenzo Musetti | 6-1,7-6 |
| Challenger de Segovia | 2019/07/31 13:10 | Khumoyun Sultanov v Antoine Escoffier | 6-1,2-6,6-7 |
| Challenger de Tampere | 2019/07/23 08:55 | Christopher O'Connell v Khumoyun Sultanov | 7-5,6-4 |
| Challenger de Nur-Sultan | 2019/07/20 08:00 | Evgeny Donskoy v Khumoyun Sultanov | 3-6,6-1,7-6 |