ATP 250 · 2021-09-27 · draw of 32
Sofia 2021
HardFinal
| 🇮🇹 Jannik Sinner | d. | 🇫🇷 Gael Monfils | 6-3 6-4 | H2H |
Semifinals
| 🇮🇹 Jannik Sinner | d. | 🇷🇸 Filip Krajinovic | 6-3 7-5 | H2H |
| 🇫🇷 Gael Monfils | d. | 🇺🇸 Marcos Giron | 7-5 6-0 | H2H |
Quarterfinals
| 🇮🇹 Jannik Sinner | d. | 🇦🇺 James Duckworth | 7-6(4) 6-4 | H2H |
| 🇷🇸 Filip Krajinovic | d. | 🇵🇱 Kamil Majchrzak | 6-3 4-6 6-3 | H2H |
| 🇺🇸 Marcos Giron | d. | 🇦🇺 John Millman | 6-4 6-2 | H2H |
| 🇫🇷 Gael Monfils | d. | 🇮🇹 Gianluca Mager | 6-2 6-2 | H2H |
Round of 16
| 🇮🇹 Jannik Sinner | d. | 🇧🇾 Egor Gerasimov | 6-2 7-6(3) | H2H |
| 🇦🇺 James Duckworth | d. | 🇫🇷 Benoit Paire | 6-4 6-4 | H2H |
| 🇵🇱 Kamil Majchrzak | d. | 🇧🇬 Dimitar Kuzmanov | 7-5 6-1 | H2H |
| 🇷🇸 Filip Krajinovic | d. | 🇷🇸 Laslo Djere | 6-3 6-0 | H2H |
| 🇦🇺 John Millman | d. | 🇺🇦 Illya Marchenko | 5-7 7-6(0) 6-3 | H2H |
| 🇺🇸 Marcos Giron | d. | 🇦🇺 Alex de Minaur | 7-6(5) 7-6(2) | H2H |
| 🇮🇹 Gianluca Mager | d. | 🇷🇸 Miomir Kecmanovic | 7-6(3) 6-3 | H2H |
| 🇫🇷 Gael Monfils | d. | 🇧🇾 Ilya Ivashka | W/O | H2H |
Round of 32
| 🇧🇾 Egor Gerasimov | d. | 🇨🇦 Vasek Pospisil | 5-7 7-6(8) 6-3 | H2H |
| 🇦🇺 James Duckworth | d. | 🇫🇮 Emil Ruusuvuori | 3-6 6-4 6-4 | H2H |
| 🇫🇷 Benoit Paire | d. | 🇪🇸 Alejandro Davidovich Fokina | 6-4 7-5 | H2H |
| 🇧🇬 Dimitar Kuzmanov | d. | 🇮🇹 Lorenzo Musetti | 6-7(4) 7-6(3) 6-3 | H2H |
| 🇷🇸 Laslo Djere | d. | 🇪🇸 Pedro Martinez | 7-6(5) 6-3 | H2H |
| 🇷🇸 Filip Krajinovic | d. | 🇧🇬 Alexandar Lazarov | 6-0 6-3 | H2H |
| 🇦🇺 John Millman | d. | 🇸🇪 Mikael Ymer | 6-2 6-4 | H2H |
| 🇺🇦 Illya Marchenko | d. | 🇮🇹 Andreas Seppi | 6-4 6-2 | H2H |
| 🇺🇸 Marcos Giron | d. | 🇪🇸 Jaume Munar | 6-7(2) 6-1 6-4 | H2H |
| 🇮🇹 Gianluca Mager | d. | 🇫🇷 Adrian Mannarino | 6-3 6-2 | H2H |
| 🇷🇸 Miomir Kecmanovic | d. | 🇧🇬 Adrian Andreev | 7-6(7) 6-4 | H2H |
| 🇧🇾 Ilya Ivashka | d. | 🇪🇸 Pablo Andujar | 6-4 6-3 | H2H |