Stadium: Court 4 Round: 25 Ground: Clay
| ITF M15 Skopje | 2021/06/03 07:55 | Timo Legout v Nicholas David Ionel | 2-6,4-6 |
| ITF M15 Skopje | 2021/06/02 09:45 | Timo Legout v Gorazd Srbljak | 7-5,6-0 |
| French Open | 2021/05/25 16:30 | Timo Legout v Evan Furness | 2-6,1-6 |
| ITF M15 Šibenik | 2021/05/23 09:00 | Hernan Casanova v Timo Legout | 4-6,6-0,2-6 |
| ITF M15 Šibenik | 2021/05/22 12:15 | Rimpei Kawakami v Timo Legout | 6-3,4-6,5-7 |
| ITF M15 Šibenik | 2021/05/21 09:50 | Timo Legout v Dan Added | 7-5,5-7,6-4 |
| ITF M15 Šibenik | 2021/05/20 12:45 | Timo Legout v Oscar Moraing | 7-5,6-3 |
| ITF M15 Šibenik | 2021/05/19 16:20 | Aldin Setkic v Timo Legout | 6-4,4-6,6-7 |
| ITF M15 Sofie | 2021/07/05 07:00 | Denislav Prodanov v Mihnea L.S. Turcu | 6-0,6-0 |
| ITF M15 Sofie | 2021/07/04 06:30 | Obrad Markovski v Denislav Prodanov | 1-6,7-5,7-10 |
| UTR Pro Tennis Series - Pazardžik | 2021/04/03 08:30 | Denislav Prodanov v Pierre Faivre | 0-6,1-6 |
| UTR Pro Tennis Series - Pazardžik | 2021/04/02 10:00 | Jules Marie v Denislav Prodanov | 6-1,6-0 |
| ITF Bulgaria F1 Qual | 2017/05/07 09:00 | Denislav Prodanov v Radoslav Shandarov | 0-6,6-2,6-7 |