| Nov 3, 2023 | vs Novak Djokovic | Paris Masters 2023 · Quarterfinal | L 7-5 6(3)-7(7) 6-4 | match → |
| Nov 2, 2023 | vs Daniel Altmaier | Paris Masters 2023 · R16 | W 3-6 3-6 | match → |
| Nov 1, 2023 | vs D Thiem | Paris Masters 2023 · R32 | W 4-6 2-6 | match → |
| Oct 5, 2023 | vs Brandon Nakashima | Shanghai Masters 2023 · R64 | L 6-0 6-2 | match → |
| Aug 28, 2023 | vs Roberto Carballes Baena | US Open 2023 · R128 | L 6-3 4-6 6-3 6-2 | match → |
| Aug 17, 2023 | vs Mackenzie McDonald | Cincinnati Open 2023 · R32 | L 4-6 0-2 | match → |
| Aug 10, 2023 | vs Marcos Giron | Canadian Open 2023 · R32 | L 6-2 4-6 6-3 | match → |
| Jul 12, 2023 | vs Carlos Alcaraz | Wimbledon 2023 · Quarterfinal | L 7(7)-6(3) 6-4 6-4 | match → |
| Jul 10, 2023 | vs Grigor Dimitrov | Wimbledon 2023 · R16 | W 6-3 6(6)-7(8) 6(4)-7(7) 3-6 | match → |
| Jul 8, 2023 | vs Alejandro Davidovich Fokina | Wimbledon 2023 · R32 | W 3-6 6-4 6-3 4-6 6(8)-7(10) | match → |
| Jul 7, 2023 | vs Roberto Carballes Baena | Wimbledon 2023 · R64 | W 3-6 6(3)-7(7) 4-6 | match → |
| Jul 5, 2023 | vs George Loffhagen | Wimbledon 2023 · R128 | W 6(4)-7(7) 3-6 2-6 | match → |
| Jun 7, 2023 | vs Casper Ruud | French Open (Roland-Garros) 2023 · Quarterfinal | L 1-6 2-6 6-3 3-6 | match → |
| Jun 5, 2023 | vs Francisco Cerundolo | French Open (Roland-Garros) 2023 · R16 | W 7(7)-6(3) 3-6 6-4 1-6 7(10)-6(7) | match → |
| Jun 3, 2023 | vs Alberto Olivieri Genaro | French Open (Roland-Garros) 2023 · R32 | W 6-4 6-1 6-3 | match → |
| Jun 1, 2023 | vs Gael Monfils | French Open (Roland-Garros) 2023 · R64 | W | match → |
| May 30, 2023 | vs Christopher Eubanks | French Open (Roland-Garros) 2023 · R128 | W 6-4 3-6 7(7)-6(2) 6-2 | match → |
| May 21, 2023 | vs Daniil Medvedev | Italian Open 2023 · Final | L 5-7 5-7 | match → |
| May 20, 2023 | vs Casper Ruud | Italian Open 2023 · Semifinal | W 6(2)-7(7) 6-4 6-2 | match → |
| May 17, 2023 | vs Novak Djokovic | Italian Open 2023 · Quarterfinal | W 2-6 6-4 2-6 | match → |
| May 16, 2023 | vs Alexei Popyrin | Italian Open 2023 · R16 | W 4-6 7-5 4-6 | match → |
| May 14, 2023 | vs F Fognini | Italian Open 2023 · R32 | W 4-6 2-6 | match → |
| May 12, 2023 | vs Arthur Fils | Italian Open 2023 · R64 | W 3-6 3-6 | match → |
| Apr 30, 2023 | vs Alejandro Davidovich Fokina | Madrid Open 2023 · R32 | L 7(7)-6(1) 5-7 7(7)-6(5) | match → |
| Apr 28, 2023 | vs Alexander Bublik | Madrid Open 2023 · R64 | W 1-6 6-4 6(9)-7(11) | match → |
| Apr 23, 2023 | vs Botic Van De Zandschulp | Bavarian International 2023 · Final | W 6-4 1-6 7(7)-6(3) | match → |
| Apr 22, 2023 | vs Christopher O'Connell | Bavarian International 2023 · Semifinal | W 6-3 6-2 | match → |
| Apr 21, 2023 | vs Cristian Garin | Bavarian International 2023 · Quarterfinal | W 6-2 6-4 | match → |
| Apr 20, 2023 | vs Yannick Hanfmann | Bavarian International 2023 · R16 | W 6-3 6-4 | match → |
| Apr 16, 2023 | vs Andrey Rublev | Monte Carlo Masters 2023 · Final | L 7-5 2-6 5-7 | match → |
| Apr 16, 2023 | vs Andrey Rublev | Monte Carlo 2023 · Final | L 7-5 2-6 5-7 | match → |
| Apr 15, 2023 | vs Jannik Sinner | Monte Carlo Masters 2023 · Semifinal | W 6-1 5-7 5-7 | match → |
| Apr 15, 2023 | vs Jannik Sinner | Monte Carlo 2023 · Semifinal | W 6-1 5-7 5-7 | match → |
| Apr 14, 2023 | vs Daniil Medvedev | Monte Carlo Masters 2023 · Quarterfinal | W 3-6 4-6 | match → |
| Apr 14, 2023 | vs Daniil Medvedev | Monte Carlo 2023 · Quarterfinal | W 3-6 4-6 | match → |
| Apr 13, 2023 | vs Matteo Berrettini | Monte Carlo Masters 2023 · R16 | W | match → |
| Apr 13, 2023 | vs Matteo Berrettini | Monte Carlo 2023 · R16 | W | match → |
| Apr 12, 2023 | vs D Thiem | Monte Carlo Masters 2023 · R32 | W 2-6 4-6 | match → |
| Apr 12, 2023 | vs D Thiem | Monte Carlo 2023 · R32 | W 2-6 4-6 | match → |
| Mar 28, 2023 | vs Taylor Fritz | Miami 2023 · R16 | L 6-3 6-4 | match → |
| Mar 28, 2023 | vs Taylor Fritz | Miami Open 2023 · R16 | L 6-3 6-4 | match → |
| Mar 26, 2023 | vs Diego Schwartzman | Miami 2023 · R32 | W 4-6 2-6 | match → |
| Mar 26, 2023 | vs Diego Schwartzman | Miami Open 2023 · R32 | W 4-6 2-6 | match → |
| Mar 25, 2023 | vs Marton Fucsovics | Miami 2023 · R64 | W 3-6 5-7 | match → |
| Mar 24, 2023 | vs Marton Fucsovics | Miami Open 2023 · R64 | W 3-6 5-7 | match → |
| Mar 14, 2023 | vs Stan Wawrinka | Indian Wells 2023 · R32 | L 6-2 6(5)-7(7) 7-5 | match → |
| Mar 12, 2023 | vs Mackenzie McDonald | Indian Wells 2023 · R64 | W 5-7 3-6 | match → |
| Mar 4, 2023 | vs Alex De Minaur | Mexican Open 2023 · Semifinal | L 6-3 5-7 2-6 | match → |
| Mar 3, 2023 | vs Matteo Berrettini | Mexican Open 2023 · Quarterfinal | W 0-6 0-1 | match → |
| Mar 2, 2023 | vs Nuno Borges | Mexican Open 2023 · R16 | W 0-6 2-6 | match → |
| Feb 28, 2023 | vs Ben Shelton | Mexican Open 2023 · R32 | W 7(9)-6(7) 4-6 2-6 | match → |
| Jan 22, 2023 | vs Andrey Rublev | Australian Open 2023 · R16 | L 6-3 3-6 6-3 4-6 7(11)-6(9) | match → |
| Jan 20, 2023 | vs Ugo Humbert | Australian Open 2023 · R32 | W 4-6 2-6 6(5)-7(7) | match → |
| Jan 18, 2023 | vs Maxime Cressy | Australian Open 2023 · R64 | W 5-7 4-6 4-6 | match → |
| Jan 16, 2023 | vs F Krajinovic | Australian Open 2023 · R128 | W 2-6 3-6 4-6 | match → |
| — | vs TBD | Shanghai Masters 2023 · R128 | W | match → |
| — | vs TBD | Miami 2023 · R128 | W | match → |
| — | vs TBD | Indian Wells 2023 · R128 | W | match → |
| — | vs TBD | Cincinnati Open 2023 · R64 | W | match → |
| — | vs TBD | Paris Masters 2023 · R64 | W | match → |
| — | vs TBD | Monte Carlo 2023 · R64 | W | match → |
