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| Oct 22 • 19:00 | Taylor Harry Fritz |  | - |  | Laslo Djere | 2 | : | 0 |
| Oct 22 • 19:00 | Denis Shapovalov |  | - |  | Marin Čilić | 0 | : | 2 |
| Oct 22 • 20:45 | Marco Cecchinato |  | - |  | Henri Laaksonen | 0 | : | 2 |
| Oct 22 • 20:45 | Marius Copil |  | - | | Ryan Harrison | 2 | : | 0 |
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| Oct 23 • 13:00 | Alexei Popyrin |  | - | | Matthew Ebden | 2 | : | 0 |
| Oct 23 • 14:30 | Taro Daniel |  | - | | Andreas Seppi | 0 | : | 2 |
| Oct 23 • 15:00 | Maximilian Marterer |  | - |  | Daniil Medvedev | 0 | : | 2 |
| Oct 23 • 17:00 | Jan-Lennard Struff | | - | | John Millman | 2 | : | 0 |
| Oct 23 • 17:30 | Peter Gojowczyk | | - |  | Nicolás Jarry | 2 | : | 1 |
| Oct 23 • 19:00 | Roger Federer | | - | | Filip Krajinović | 2 | : | 1 |
| Oct 23 • 20:30 | Leonardo Mayer |  | - |  | Gilles Simon | 0 | : | 2 |
| Oct 24 • 13:00 | Roberto Bautista-Agut |  | - |  | João Sousa | 2 | : | 0 |
| Oct 24 • 14:30 | Dušan Lajović | | - | | Adrian Mannarino | 2 | : | 1 |
| Oct 24 • 15:00 | Ernests Gulbis |  | - | | Jack Sock | 2 | : | 0 |
| Oct 24 • 17:00 | Stefanos Tsitsipas |  | - | | Jérémy Chardy | 2 | : | 0 |
| Oct 24 • 19:00 | Robin Haase |  | - | | Alexander Zverev | 0 | : | 2 |
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| Oct 24 • 20:30 | Marius Copil | | - | | Marin Čilić | 2 | : | 0 |
| Oct 24 • 21:00 | Henri Laaksonen | | - | | Taylor Harry Fritz | 0 | : | 2 |
| Oct 25 • 13:00 | Andreas Seppi | | - | | Daniil Medvedev | 0 | : | 2 |
| Oct 25 • 15:00 | Stefanos Tsitsipas | | - | | Peter Gojowczyk | 2 | : | 0 |
| Oct 25 • 15:00 | Roberto Bautista-Agut | | - | | Dušan Lajović | 2 | : | 1 |
| Oct 25 • 17:00 | Alexei Popyrin | | - | | Alexander Zverev | 0 | : | 2 |
| Oct 25 • 19:00 | Roger Federer | | - | | Jan-Lennard Struff | 2 | : | 0 |
| Oct 25 • 20:30 | Gilles Simon | | - | | Ernests Gulbis | 2 | : | 0 |
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| Oct 26 • 15:00 | Taylor Harry Fritz | | - | | Marius Copil | 0 | : | 2 |
| Oct 26 • 17:00 | Roberto Bautista-Agut | | - | | Alexander Zverev | 0 | : | 2 |
| Oct 26 • 19:00 | Roger Federer | | - | | Gilles Simon | 2 | : | 1 |
| Oct 26 • 20:30 | Stefanos Tsitsipas | | - | | Daniil Medvedev | 1 | : | 2 |
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| Oct 27 • 14:30 | Marius Copil | | - | | Alexander Zverev | 2 | : | 1 |
| Oct 27 • 16:00 | Roger Federer | | - | | Daniil Medvedev | 2 | : | 0 |
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| Oct 28 • 15:00 | Roger Federer | | - | | Marius Copil | 2 | : | 0 |
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