Stadium: Center Court Round: 26 Ground: Clay
| Challenger Tampere | 2021/07/19 15:30 | Kimmer Coppejans v Dimitar Kuzmanov | 6-1,3-6,6-7 |
| Iasi, Romania | 2021/07/16 09:40 | Felipe Meligeni Rodrigues Alves v Dimitar Kuzmanov | 6-0,3-6,6-3 |
| Iasi, Romania | 2021/07/14 11:15 | Nicholas David Ionel v Dimitar Kuzmanov | 6-2,3-6,4-6 |
| Iasi, Romania | 2021/07/13 07:00 | Krstin, Pedja v Dimitar Kuzmanov | 2-6,2-6 |
| Challenger Perugia | 2021/07/07 13:50 | Dimitar Kuzmanov v Nerman Fatic | 4-6,6-7 |
| Challenger Perugia | 2021/07/05 19:00 | Federico Gaio v Dimitar Kuzmanov | 6-2,3-6,6-7 |
| Wimbledon, London, Great Britain | 2021/06/22 10:00 | Marius Copil v Dimitar Kuzmanov | 6-4,6-3 |
| Challenger Almaty | 2021/06/11 04:30 | Chun Hsin Tseng v Dimitar Kuzmanov | 7-6,6-3 |
| Challenger Tampere | 2021/07/19 10:40 | Kyrian Jacquet v Nicolas Kicker | 4-6,7-6,2-6 |
| Challenger Tampere | 2021/07/18 10:20 | Kyrian Jacquet v Luca Castelnuovo | 6-7,6-1,6-0 |
| ITF M25 Marburg | 2021/07/06 16:15 | Max Wiskandt v Kyrian Jacquet | 6-2,6-4 |
| ITF M25 Bourg-en-Bresse | 2021/06/30 15:45 | Kyrian Jacquet v Jakub Paul | 1-6,5-7 |
| Challenger - Aix en Provence | 2021/06/19 13:15 | Carlos Taberner v Kyrian Jacquet | 6-3,6-7,6-0 |
| Challenger - Aix en Provence | 2021/06/18 12:30 | Kyrian Jacquet v Titouan Droguet | 7-5,6-3 |
| Challenger - Aix en Provence | 2021/06/17 09:00 | Juan Pablo Varillas v Kyrian Jacquet | 4-6,3-6 |
| Challenger - Aix en Provence | 2021/06/15 11:20 | Maxime Janvier v Kyrian Jacquet | 3-6,6-7 |