Stadium: Court 5 Round: 25 Ground: Hardcourt outdoor
| Challenger St. Petersburg | 2021/03/06 09:00 | Altug Celikbilek v Artem Dubrivnyy | 5-7,6-2,6-3 |
| Challenger St. Petersburg | 2021/03/05 08:00 | Artem Dubrivnyy v Andrey Kuznetsov | 6-3,6-7,6-3 |
| Challenger St. Petersburg | 2021/03/03 12:15 | Viktor Durasovic v Artem Dubrivnyy | 5-7,6-3,3-6 |
| Challenger St. Petersburg | 2021/03/02 09:45 | Igor Sijsling v Artem Dubrivnyy | 6-3,4-6,3-6 |
| Challenger St. Petersburg | 2021/03/01 08:30 | Artem Dubrivnyy v Skander Mansouri | 4-6,7-6,6-0 |
| Challenger St. Petersburg | 2021/02/28 10:45 | Konstantin Kravchuk v Artem Dubrivnyy | 6-7,4-6 |
| ITF M15 St Petersburg | 2021/02/11 08:30 | Artem Dubrivnyy v Martin Krumich | 4-6,6-1,5-7 |
| ITF M15 St Petersburg | 2021/02/10 06:50 | Artem Dubrivnyy v Maxim Ratniuk | 6-2,6-3 |
| Challenger Potchefstroom | 2021/02/15 13:05 | Jay Clarke v Dimitar Kuzmanov | 7-5,3-6,6-7 |
| Challenger Potchefstroom | 2021/02/09 14:45 | Jay Clarke v Ulises Blanch | 6-7,4-6 |
| Challenger Istanbul | 2021/01/19 11:20 | Jay Clarke v Federico Gaio | 3-6,5-7 |
| Challenger Istanbul | 2021/01/18 08:15 | Denis Istomin v Jay Clarke | 6-7,6-3,4-6 |
| Challenger Istanbul | 2021/01/17 11:15 | Malek Jaziri v Jay Clarke | 6-7,6-2,3-6 |
| Australian Open | 2021/01/10 10:10 | Tung-Lin Wu v Jay Clarke | 6-2,6-4 |
| Battle of the Brits | 2020/12/22 11:30 | Jack Draper v Jay Clarke | 6-4,6-1 |
| Challenger Ortisei | 2020/11/18 10:00 | Alexandre Muller v Jay Clarke | 7-6,6-7,6-3 |