Stadium: Centre Court Round: 26 Ground: Hardcourt outdoor
| Mubadala World Tennis Championship | 2021/12/17 13:00 | Andrey Rublev v Denis Shapovalov | 7-6,3-6,6-4 |
| Mubadala World Tennis Championship | 2021/12/16 12:00 | Taylor Fritz v Denis Shapovalov | 3-6,0-6 |
| ATP Stockholm | 2021/11/13 15:00 | Tommy Paul v Denis Shapovalov | 6-4,2-6,6-4 |
| ATP Stockholm | 2021/11/12 19:50 | Denis Shapovalov v Felix Auger Aliassime | 6-4,7-5 |
| ATP Stockholm | 2021/11/11 19:35 | Arthur Rinderknech v Denis Shapovalov | 6-4,3-6,5-7 |
| ATP Stockholm | 2021/11/10 12:50 | Andrea Vavassori v Denis Shapovalov | 6-7,1-6 |
| ATP St Petersburg | 2021/10/29 11:30 | Jan-Lennard Struff v Denis Shapovalov | 6-4,6-3 |
| ATP St Petersburg | 2021/10/27 10:00 | Pablo Andujar v Denis Shapovalov | 6-2,3-6,0-6 |
| Challenger Helsinki | 2021/11/21 11:00 | Alex Molcan v Joao Sousa | 6-3,6-2 |
| Challenger Helsinki | 2021/11/20 11:35 | Alexander Shevchenko v Alex Molcan | 2-6,6-7 |
| Challenger Helsinki | 2021/11/19 12:30 | Alex Molcan v Oscar Otte | 6-3,4-6,6-1 |
| Challenger Helsinki | 2021/11/18 11:30 | Alex Molcan v Shintaro Mochizuki | 6-3,6-2 |
| Challenger Helsinki | 2021/11/17 11:30 | Alex Molcan v Tim Van Rijthoven | 6-4,0-6,7-6 |
| Challenger Bratislava | 2021/11/13 14:00 | Alex Molcan v Tallon Griekspoor | 7-6,3-6,4-6 |
| Challenger Bratislava | 2021/11/12 16:00 | Alex Molcan v Damir Dzumhur | 6-1,4-6,6-3 |
| Challenger Bratislava | 2021/11/11 16:00 | Alex Molcan v Tobias Kamke | 6-2,6-2 |