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| Sep 20 • 13:00 | Dominic Thiem |  | - |  | Denis Shapovalov | 2 | : | 1 |
| Sep 20 • 14:30 | Fabio Fognini |  | - |  | Jack Sock | 0 | : | 2 |
| Sep 20 • 19:00 | Stefanos Tsitsipas |  | - | | Taylor Harry Fritz | 2 | : | 1 |
| Sep 20 • 20:30 | Federer + Zverev |  | - |  | Shapovalov + Sock | 2 | : | 0 |
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| Sep 21 • 13:00 | Alexander Zverev |  | - | | John Isner | 1 | : | 2 |
| Sep 21 • 14:30 | Roger Federer |  | - |  | Nick Kyrgios | 2 | : | 1 |
| Sep 21 • 19:00 | Rafael Nadal |  | - | | Milos Raonic | 2 | : | 0 |
| Sep 21 • 20:30 | Nadal + Tsitsipas | | - | | Kyrgios + Sock | 1 | : | 2 |
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| Sep 22 • 12:00 | Federer + Tsitsipas | | - | | Isner + Sock | 1 | : | 2 |
| Sep 22 • 13:30 | Dominic Thiem | | - | | Nick Kyrgios | 0 | : | 0 |
| Sep 22 • 15:00 | Roger Federer | | - | | John Isner | 2 | : | 0 |
| Sep 22 • 18:00 | Alexander Zverev | | - | | Milos Raonic | 2 | : | 1 |
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