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| Oct 12 • 12:00 | Tennys Sandgren |  | - |  | Aslan Karatsev | 1 | : | 2 |
| Oct 12 • 13:00 | Taylor Harry Fritz | | - |  | Cameron Norrie | 1 | : | 2 |
| Oct 12 • 13:30 | Alexander Bublik |  | - | | Mackenzie McDonald | 2 | : | 1 |
| Oct 12 • 16:10 | Evgeny Donskoy | | - |  | Egor Gerasimov | 2 | : | 0 |
| Oct 12 • 18:30 | Stanislas Wawrinka |  | - | | Daniel Evans | 2 | : | 1 |
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| Oct 13 • 12:00 | Feliciano López |  | - |  | Borna Ćorić | 0 | : | 2 |
| Oct 13 • 12:00 | Adrian Mannarino |  | - | | Ilya Ivashka | 0 | : | 2 |
| Oct 13 • 13:30 | Jeffrey John Wolf | | - |  | Milos Raonic | 0 | : | 2 |
| Oct 13 • 13:30 | Mikhail Kukushkin | | - |  | Miomir Kecmanovic | 0 | : | 2 |
| Oct 13 • 15:00 | Karen Khachanov | | - |  | James Duckworth | 2 | : | 0 |
| Oct 13 • 17:30 | Vasek Pospisil | | - | | Andrey Rublev | 0 | : | 2 |
| Oct 14 • 12:00 | Nino Serdarusic | | - | | Reilly Opelka | 1 | : | 2 |
| Oct 14 • 12:00 | Viktor Troicki | | - | | Denis Shapovalov | 0 | : | 2 |
| Oct 14 • 13:30 | Roman Safiullin | | - |  | Emilio Gómez | 2 | : | 0 |
| Oct 14 • 15:30 | Pavel Kotov | | - | | Ugo Humbert | 1 | : | 2 |
| Oct 14 • 17:30 | Daniil Medvedev | | - | | Richard Gasquet | 2 | : | 1 |
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| Oct 14 • 13:30 | Cameron Norrie | | - | | Miomir Kecmanovic | 2 | : | 1 |
| Oct 14 • 19:00 | Stanislas Wawrinka | | - | | Evgeny Donskoy | 2 | : | 1 |
| Oct 15 • 12:00 | Roman Safiullin | | - | | Borna Ćorić | 0 | : | 2 |
| Oct 15 • 12:00 | Ilya Ivashka | | - | | Denis Shapovalov | 0 | : | 2 |
| Oct 15 • 13:30 | Ugo Humbert | | - | | Andrey Rublev | 1 | : | 2 |
| Oct 15 • 15:00 | Daniil Medvedev | | - | | Reilly Opelka | 1 | : | 2 |
| Oct 15 • 17:30 | Karen Khachanov | | - | | Aslan Karatsev | 2 | : | 1 |
| Oct 15 • 19:00 | Alexander Bublik | | - | | Milos Raonic | 0 | : | 2 |
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| Oct 16 • 12:00 | Cameron Norrie | | - | | Andrey Rublev | 0 | : | 2 |
| Oct 16 • 13:30 | Stanislas Wawrinka | | - | | Denis Shapovalov | 0 | : | 2 |
| Oct 16 • 15:00 | Reilly Opelka | | - | | Borna Ćorić | 0 | : | 2 |
| Oct 16 • 17:30 | Karen Khachanov | | - | | Milos Raonic | 0 | : | 2 |
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| Oct 17 • 13:00 | Andrey Rublev | | - | | Denis Shapovalov | 2 | : | 1 |
| Oct 17 • 14:30 | Borna Ćorić | | - | | Milos Raonic | 2 | : | 1 |
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| Oct 18 • 15:30 | Borna Ćorić | | - | | Andrey Rublev | 0 | : | 2 |
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St. Petersburg Open 2020
