| Novak Djokovic (1) | Bye | | | | | | |
| Bye | - | Novak Djokovic (1) | 7(7) 6 | | | | |
| Bernard Tomic | 6 6 | Bernard Tomic | 6(2) 2 | | | | |
| Thiago Monteiro | 4 1 | | | Novak Djokovic (1) | 7 4 6 | | |
| Peter Gojowczyk | 4 2 | | | Federico Delbonis | 5 6 1 | | |
| Federico Delbonis | 6 6 | Federico Delbonis | 7 3 7(7) | | | | |
| Bye | - | John Millman (32) | 5 6 6(2) | | | | |
| John Millman (32) | Bye | | | | | Novak Djokovic (1) | 6 5 3 |
| Roberto Bautista Agut (22) | Bye | | | | | Roberto Bautista Agut (22) | 1 7 6 |
| Bye | - | Roberto Bautista Agut (22) | 7(7) 6 | | | | |
| Janko Tipsarevic | 6 6 | Janko Tipsarevic | 6(3) 4 | | | | |
| Bradley Klahn | 3 3 | | | Roberto Bautista Agut (22) | 6 6 | | |
| Mikhail Kukushkin | 6(3) 4 | | | Fabio Fognini (15) | 4 4 | | |
| Guido Andreozzi | 7(7) 6 | Guido Andreozzi | 7 4 4 | | | | |
| Bye | - | Fabio Fognini (15) | 5 6 6 | | | | |
| Fabio Fognini (15) | Bye | | | | | | |
| Milos Raonic (12) | Bye | | | | | | |
| Bye | - | Milos Raonic (12) | WO | | | | |
| Maximilian Marterer | 6 3 6 | Maximilian Marterer | | | | | |
| Taylor Fritz | 4 6 3 | | | Milos Raonic (12) | 4 4 | | |
| Thomas Fabbiano | 4 6 3 | | | Kyle Edmund (19) | 6 6 | | |
| Ilya Ivashka | 6 1 6 | Ilya Ivashka | 3 2 | | | | |
| Bye | - | Kyle Edmund (19) | 6 6 | | | | |
| Kyle Edmund (19) | Bye | | | | | Kyle Edmund (19) | 6(5) 6(3) |
| Lucas Pouille (25) | Bye | | | | | John Isner (7) | 7(7) 7(7) |
| Bye | - | Lucas Pouille (25) | 6 4 3 | | | | |
| Marius Copil | 4 2 | Albert Ramos-Vinolas | 4 6 6 | | | | |
| Albert Ramos-Vinolas | 6 6 | | | Albert Ramos-Vinolas | 5 6(6) | | |
| Martin Klizan | 4 3 | | | John Isner (7) | 7 7(8) | | |
| Lorenzo Sonego | 6 6 | Lorenzo Sonego | 6(2) 6(7) | | | | |
| Bye | - | John Isner (7) | 7(7) 7(9) | | | | |
| John Isner (7) | Bye | | | | | | |
| Dominic Thiem (3) | Bye | | | | | | |
| Bye | - | Dominic Thiem (3) | 4 4 | | | | |
| Matteo Berrettini | 4 3 | Hubert Hurkacz | 6 6 | | | | |
| Hubert Hurkacz | 6 6 | | | Hubert Hurkacz | 6(5) 4 | | |
| Felix Auger-Aliassime | 3 6 6 | | | Felix Auger-Aliassime | 7(7) 6 | | |
| Casper Ruud | 6 1 2 | Felix Auger-Aliassime | 6 4 6 | | | | |
| Bye | - | Marton Fucsovics (29) | 4 6 0 | | | | |
| Marton Fucsovics (29) | Bye | | | | | Felix Auger-Aliassime | 7(7) 6 |
| Nikoloz Basilashvili (17) | Bye | | | | | Nikoloz Basilashvili (17) | 6(4) 4 |
| Bye | - | Nikoloz Basilashvili (17) | 6 6 | | | | |
| Nicola Kuhn | 6 5 2 ret. | Mischa Zverev | 3 2 | | | | |
| Mischa Zverev | 4 7 2 | | | Nikoloz Basilashvili (17) | 7(7) 6 | | |
| Robin Haase | 6 6 | | | Robin Haase | 6(3) 3 | | |
| Lukas Lacko | 2 4 | Robin Haase | 3 6 6 | | | | |
| Bye | - | Lloyd Harris | 6 3 4 | | | | |
| Lloyd Harris | Bye | | | | | | |
| Borna Coric (11) | Bye | | | | | | |
| Bye | - | Borna Coric (11) | 7(9) 0 6 | | | | |
| Roberto Carballes Baena | 6 6 | Roberto Carballes Baena | 6(7) 6 2 | | | | |
| Denis Kudla | 1 2 | | | Borna Coric (11) | 6(2) 6 6 | | |
| Jeremy Chardy | 6(1) 6 7(7) | | | Jeremy Chardy | 7(7) 2 3 | | |
| Nicolas Jarry | 7(7) 2 6(5) | Jeremy Chardy | 6 6 | | | | |
| Bye | - | Gilles Simon (23) | 4 2 | | | | |
| Gilles Simon (23) | Bye | | | | | Borna Coric (11) | 4 6 6 |
| Nick Kyrgios (27) | Bye | | | | | Nick Kyrgios (27) | 6 3 2 |
| Bye | - | Nick Kyrgios (27) | 7 6 | | | | |
| Tennys Sandgren | 7 4 6(5) | Alexander Bublik | 5 3 | | | | |
| Alexander Bublik | 5 6 7(7) | | | Nick Kyrgios (27) | 6 6 | | |
| Dusan Lajovic | 6 6(6) 6 | | | Dusan Lajovic | 3 1 | | |
| Pablo Cuevas | 4 7(8) 3 | Dusan Lajovic | 2 6 6 | | | | |
| Bye | - | Kei Nishikori (5) | 6 2 3 | | | | |
| Kei Nishikori (5) | Bye | | | | | | |
| Kevin Anderson (6) | Bye | | | | | | |
| Bye | - | Kevin Anderson (6) | 6 3 6 | | | | |
| Jaume Munar | 7(7) 6 | Jaume Munar | 4 6 3 | | | | |
| Prajnesh Gunneswaran | 6(3) 4 | | | Kevin Anderson (6) | 6 7(8) | | |
| Joao Sousa | 6 7 | | | Joao Sousa | 4 6(6) | | |
| Chun-Hsin Tseng | 4 5 | Joao Sousa | 7(8) 6 | | | | |
| Bye | - | Steve Johnson (31) | 6(6) 4 | | | | |
| Steve Johnson (31) | Bye | | | | | Kevin Anderson (6) | 7 7 |
| Grigor Dimitrov (24) | Bye | | | | | Jordan Thompson | 5 5 |
| Bye | - | Grigor Dimitrov (24) | 6 6 | | | | |
| Feliciano Lopez | 7 4 6 | Feliciano Lopez | 1 3 | | | | |
| Benoit Paire | 5 6 4 | | | Grigor Dimitrov (24) | 5 5 | | |
| Cameron Norrie | 6 6(5) 3 | | | Jordan Thompson | 7 7 | | |
| Jordan Thompson | 4 7(7) 6 | Jordan Thompson | 6 6 | | | | |
| Bye | - | Karen Khachanov (10) | 2 3 | | | | |
| Karen Khachanov (10) | Bye | | | | | | |
| Daniil Medvedev (13) | Bye | | | | | | |
| Bye | - | Daniil Medvedev (13) | 6 6 | | | | |
| Adrian Mannarino | 4 6 6 | Adrian Mannarino | 2 1 | | | | |
| Aljaz Bedene | 6 4 2 | | | Daniil Medvedev (13) | 7(7) 6(5) 7(7) | | |
| Reilly Opelka | 4 6 6 | | | Reilly Opelka | 6(5) 7(7) 6(0) | | |
| Jan-Lennard Struff | 6 3 4 | Reilly Opelka | 6 3 6 | | | | |
| Bye | - | Diego Schwartzman (21) | 4 6 4 | | | | |
| Diego Schwartzman (21) | Bye | | | | | Daniil Medvedev (13) | 4 2 |
| Stan Wawrinka (30) | Bye | | | | | Roger Federer (4) | 6 6 |
| Bye | - | Stan Wawrinka (30) | 7 2 6(5) | | | | |
| Pierre-Hugues Herbert | 4 4 | Filip Krajinovic | 5 6 7(7) | | | | |
| Filip Krajinovic | 6 6 | | | Filip Krajinovic | 5 3 | | |
| Radu Albot | 6 3 | | | Roger Federer (4) | 7 6 | | |
| Matthew Ebden | 0 2 ret. | Radu Albot | 6 5 3 | | | | |
| Bye | - | Roger Federer (4) | 4 7 6 | | | | |
| Roger Federer (4) | Bye | | | | | | |
| Stefanos Tsitsipas (8) | Bye | | | | | | |
| Bye | - | Stefanos Tsitsipas (8) | 7(7) 6 | | | | |
| Mackenzie McDonald | 6 6(4) 7(7) | Mackenzie McDonald | 6(4) 1 | | | | |
| Ugo Humbert | 4 7(7) 6(4) | | | Stefanos Tsitsipas (8) | 6 6 | | |
| Leonardo Mayer | 4 6 6 | | | Leonardo Mayer | 4 4 | | |
| Mikael Ymer | 6 3 4 | Leonardo Mayer | 6 6 | | | | |
| Bye | - | Guido Pella (26) | 2 4 | | | | |
| Guido Pella (26) | Bye | | | | | Stefanos Tsitsipas (8) | 6 3 6(3) |
| Denis Shapovalov (20) | Bye | | | | | Denis Shapovalov (20) | 4 6 7(7) |
| Bye | - | Denis Shapovalov (20) | 4 6 6 | | | | |
| Daniel Evans | 6 6 | Daniel Evans | 6 1 3 | | | | |
| Malek Jaziri | 2 0 | | | Denis Shapovalov (20) | 6 7(7) | | |
| Andrey Rublev | 3 6 6 | | | Andrey Rublev | 3 6(5) | | |
| Taro Daniel | 6 3 4 | Andrey Rublev | 6 6 | | | | |
| Bye | - | Marin Cilic (9) | 4 4 | | | | |
| Marin Cilic (9) | Bye | | | | | | |
| Marco Cecchinato (14) | Bye | | | | | | |
| Bye | - | Marco Cecchinato (14) | WO | | | | |
| Christopher Eubanks | 6 4 6(5) | Damir Dzumhur | | | | | |
| Damir Dzumhur | 1 6 7(7) | | | Marco Cecchinato (14) | 4 4 | | |
| Pablo Andujar | 7(7) 6 | | | David Goffin (18) | 6 6 | | |
| Ivo Karlovic | 6(2) 4 | Pablo Andujar | 4 1 | | | | |
| Bye | - | David Goffin (18) | 6 6 | | | | |
| David Goffin (18) | Bye | | | | | David Goffin (18) | 5 6(6) |
| Frances Tiafoe (28) | Bye | | | | | Frances Tiafoe (28) | 7 7(8) |
| Bye | - | Frances Tiafoe (28) | 7(8) 7(7) | | | | |
| Ernests Gulbis | 2 5 | Miomir Kecmanovic | 6(6) 6(5) | | | | |
| Miomir Kecmanovic | 6 7 | | | Frances Tiafoe (28) | 5 6 6 | | |
| Sam Querrey | 3 2 | | | David Ferrer | 7 3 3 | | |
| David Ferrer | 6 6 | David Ferrer | 2 7 6 | | | | |
| Bye | - | Alexander Zverev (2) | 6 5 3 | | | | |
| Alexander Zverev (2) | Bye | | | | | | |
