| Nov 5, 2023 | vs Grigor Dimitrov | Paris Masters 2023 · Final | W 6-4 6-3 | match → |
| Nov 4, 2023 | vs Andrey Rublev | Paris Masters 2023 · Semifinal | W 5-7 7(7)-6(3) 7-5 | match → |
| Nov 3, 2023 | vs Holger Rune | Paris Masters 2023 · Quarterfinal | W 7-5 6(3)-7(7) 6-4 | match → |
| Nov 2, 2023 | vs Tallon Griekspoor | Paris Masters 2023 · R16 | W 4-6 7(7)-6(2) 6-4 | match → |
| Nov 1, 2023 | vs Tomas Martin Etcheverry | Paris Masters 2023 · R32 | W 6-3 6-2 | match → |
| Sep 11, 2023 | vs Daniil Medvedev | US Open 2023 · Final | W 3-6 6(5)-7(7) 3-6 | match → |
| Sep 8, 2023 | vs Ben Shelton | US Open 2023 · Semifinal | W 3-6 2-6 6(4)-7(7) | match → |
| Sep 5, 2023 | vs Taylor Fritz | US Open 2023 · Quarterfinal | W 1-6 4-6 4-6 | match → |
| Sep 4, 2023 | vs Borna Gojo | US Open 2023 · R16 | W 2-6 5-7 4-6 | match → |
| Sep 2, 2023 | vs Laslo Djere | US Open 2023 · R32 | W 6-4 6-4 1-6 1-6 3-6 | match → |
| Aug 30, 2023 | vs Bernabe Zapata Miralles | US Open 2023 · R64 | W 4-6 1-6 1-6 | match → |
| Aug 29, 2023 | vs Alexandre Muller | US Open 2023 · R128 | W 0-6 2-6 3-6 | match → |
| Aug 21, 2023 | vs Carlos Alcaraz | Cincinnati Open 2023 · Final | W 7-5 6(7)-7(9) 6(4)-7(7) | match → |
| Aug 20, 2023 | vs Alexander Zverev | Cincinnati Open 2023 · Semifinal | W 6(5)-7(7) 5-7 | match → |
| Aug 19, 2023 | vs Taylor Fritz | Cincinnati Open 2023 · Quarterfinal | W 0-6 4-6 | match → |
| Aug 18, 2023 | vs Gael Monfils | Cincinnati Open 2023 · R16 | W 3-6 2-6 | match → |
| Aug 17, 2023 | vs Alejandro Davidovich Fokina | Cincinnati Open 2023 · R32 | W 4-6 0-0 | match → |
| Jul 16, 2023 | vs Carlos Alcaraz | Wimbledon 2023 · Final | L 1-6 7(8)-6(6) 6-1 3-6 6-4 | match → |
| Jul 14, 2023 | vs Jannik Sinner | Wimbledon 2023 · Semifinal | W 3-6 4-6 6(4)-7(7) | match → |
| Jul 11, 2023 | vs Andrey Rublev | Wimbledon 2023 · Quarterfinal | W 6-4 1-6 4-6 3-6 | match → |
| Jul 10, 2023 | vs Hubert Hurkacz | Wimbledon 2023 · R16 | W 6(6)-7(8) 6(6)-7(8) 7-5 4-6 | match → |
| Jul 7, 2023 | vs Stan Wawrinka | Wimbledon 2023 · R32 | W 3-6 1-6 6(5)-7(7) | match → |
| Jul 5, 2023 | vs Jordan Thompson | Wimbledon 2023 · R64 | W 3-6 6(4)-7(7) 5-7 | match → |
| Jul 3, 2023 | vs Pedro Cachin | Wimbledon 2023 · R128 | W 3-6 3-6 6(4)-7(7) | match → |
| Jun 11, 2023 | vs Casper Ruud | French Open (Roland-Garros) 2023 · Final | W 7(7)-6(1) 6-3 7-5 | match → |
| Jun 9, 2023 | vs Carlos Alcaraz | French Open (Roland-Garros) 2023 · Semifinal | W 3-6 7-5 1-6 1-6 | match → |
| Jun 6, 2023 | vs Karen Khachanov | French Open (Roland-Garros) 2023 · Quarterfinal | W 4-6 7(7)-6(0) 6-2 6-4 | match → |
| Jun 4, 2023 | vs Pablo Varillas Juan | French Open (Roland-Garros) 2023 · R16 | W 6-3 6-2 6-2 | match → |
| Jun 2, 2023 | vs Alejandro Davidovich Fokina | French Open (Roland-Garros) 2023 · R32 | W 7(7)-6(4) 7(7)-6(5) 6-2 | match → |
| May 31, 2023 | vs Marton Fucsovics | French Open (Roland-Garros) 2023 · R64 | W 7(7)-6(2) 6-0 6-3 | match → |
| May 29, 2023 | vs Aleksandar Kovacevic | French Open (Roland-Garros) 2023 · R128 | W 6-3 6-2 7(7)-6(1) | match → |
| May 17, 2023 | vs Holger Rune | Italian Open 2023 · Quarterfinal | L 2-6 6-4 2-6 | match → |
| May 16, 2023 | vs Cameron Norrie | Italian Open 2023 · R16 | W 6-3 6-4 | match → |
| May 14, 2023 | vs Grigor Dimitrov | Italian Open 2023 · R32 | W 6-3 4-6 6-1 | match → |
| May 12, 2023 | vs Tomas Martin Etcheverry | Italian Open 2023 · R64 | W 7(7)-6(5) 6-2 | match → |
| Apr 13, 2023 | vs Lorenzo Musetti | Monte Carlo Masters 2023 · R16 | L 6-4 5-7 4-6 | match → |
| Apr 13, 2023 | vs Lorenzo Musetti | Monte Carlo 2023 · R16 | L 6-4 5-7 4-6 | match → |
| Apr 11, 2023 | vs Ivan Gakhov | Monte Carlo Masters 2023 · R32 | W 7(7)-6(5) 6-2 | match → |
| Apr 11, 2023 | vs Ivan Gakhov | Monte Carlo 2023 · R32 | W 7(7)-6(5) 6-2 | match → |
| Mar 3, 2023 | vs Daniil Medvedev | Dubai Championships 2023 · Semifinal | L 4-6 4-6 | match → |
| Mar 2, 2023 | vs Hubert Hurkacz | Dubai Championships 2023 · Quarterfinal | W 6-3 7-5 | match → |
| Mar 1, 2023 | vs Tallon Griekspoor | Dubai Championships 2023 · R16 | W 6-2 6-3 | match → |
| Feb 28, 2023 | vs Tomas Machac | Dubai Championships 2023 · R32 | W 6-3 3-6 7(7)-6(1) | match → |
| Jan 28, 2023 | vs Stefanos Tsitsipas | Australian Open 2023 · Final | W 3-6 6(4)-7(7) 6(5)-7(7) | match → |
| Jan 26, 2023 | vs Tommy Paul | Australian Open 2023 · Semifinal | W 7-5 6-1 6-2 | match → |
| Jan 24, 2023 | vs Andrey Rublev | Australian Open 2023 · Quarterfinal | W 1-6 2-6 4-6 | match → |
| Jan 22, 2023 | vs Alex De Minaur | Australian Open 2023 · R16 | W 2-6 1-6 2-6 | match → |
| Jan 20, 2023 | vs Grigor Dimitrov | Australian Open 2023 · R32 | W 6(7)-7(9) 3-6 4-6 | match → |
| Jan 18, 2023 | vs Enzo Couacaud | Australian Open 2023 · R64 | W 1-6 7(7)-6(5) 2-6 0-6 | match → |
| Jan 17, 2023 | vs Roberto Carballes Baena | Australian Open 2023 · R128 | W 3-6 4-6 0-6 | match → |
| — | vs TBD | Monte Carlo 2023 · R64 | W | match → |
| — | vs TBD | Cincinnati Open 2023 · R64 | W | match → |
| — | vs TBD | Paris Masters 2023 · R64 | W | match → |
