| Player 1 | Result | Player 2 |
|---|---|---|
| 🎾 Center court | ||
| Jannik Sinner (1) [Italy] | 3-6 5-7 2-2 Walkover | Grigor Dimitrov (19) [Bulgaria] |
| Alex de Minaur (11) [Australia] | 6-1 4-6 4-6 4-6 Finished | Novak Djokovic (6) [Serbia] |
| 🎾 Court 1 | ||
| Ben Shelton (10) [United States] | 3-6 6-1 7-6 7-5 Finished | Lorenzo Sonego [Italy] |
| 🎾 Court 2 | ||
| Marin Čilić [Croatia] | 4-6 4-6 7-6 6-7 Finished | Flavio Cobolli (22) [Italy] |