ATP 250 · 1999-08-23 · draw of 32
Boston 1999
HardFinal
| 🇷🇺 Marat Safin | d. | 🇬🇧 Greg Rusedski | 6-4 7-6(11) | H2H |
Semifinals
| 🇷🇺 Marat Safin | d. | 🇳🇱 Sjeng Schalken | 5-7 6-3 6-1 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇫🇷 Arnaud Clement | 6-4 5-7 6-2 | H2H |
Quarterfinals
| 🇳🇱 Sjeng Schalken | d. | 🇨🇱 Marcelo Rios | 7-5 6-0 | H2H |
| 🇷🇺 Marat Safin | d. | 🇩🇪 David Prinosil | 6-4 6-2 | H2H |
| 🇫🇷 Arnaud Clement | d. | 🇫🇷 Sebastien Grosjean | 1-6 6-4 6-3 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇸🇪 Jonas Bjorkman | 7-5 6-3 | H2H |
Round of 16
| 🇨🇱 Marcelo Rios | d. | 🇨🇦 Daniel Nestor | 6-7(6) 6-2 6-4 | H2H |
| 🇳🇱 Sjeng Schalken | d. | 🇦🇲 Sargis Sargsian | 6-2 6-3 | H2H |
| 🇩🇪 David Prinosil | d. | 🇫🇷 Cedric Pioline | 7-6(1) 6-3 | H2H |
| 🇷🇺 Marat Safin | d. | 🇺🇸 Bob Bryan | 6-4 7-6(3) | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇦🇺 Andrew Ilie | W/O | H2H |
| 🇫🇷 Arnaud Clement | d. | 🇪🇸 Felix Mantilla | 6-2 6-1 | H2H |
| 🇸🇪 Jonas Bjorkman | d. | 🇵🇭 Cecil Mamiit | 6-0 6-7(3) 7-6(6) | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇬🇷 Solon Peppas | 6-3 6-3 | H2H |
Round of 32
| 🇨🇱 Marcelo Rios | d. | 🇺🇸 James Blake | 6-3 7-6(4) | H2H |
| 🇨🇦 Daniel Nestor | d. | 🇦🇷 Martin Rodriguez | 6-2 6-2 | H2H |
| 🇳🇱 Sjeng Schalken | d. | 🇳🇱 Paul Haarhuis | 4-6 6-3 6-0 | H2H |
| 🇦🇲 Sargis Sargsian | d. | 🇺🇸 Jim Courier | 6-4 6-4 | H2H |
| 🇫🇷 Cedric Pioline | d. | 🇦🇷 Gaston Gaudio | 6-4 6-0 | H2H |
| 🇩🇪 David Prinosil | d. | 🇺🇸 Jim Thomas | 6-2 6-1 | H2H |
| 🇺🇸 Bob Bryan | d. | 🇦🇹 Markus Hipfl | 6-3 6-2 | H2H |
| 🇷🇺 Marat Safin | d. | 🇮🇹 Gianluca Pozzi | 7-5 7-5 | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇫🇷 Guillaume Raoux | 6-4 3-6 6-3 | H2H |
| 🇦🇺 Andrew Ilie | d. | 🇷🇴 Andrei Pavel | 6-3 1-0 RET | H2H |
| 🇫🇷 Arnaud Clement | d. | 🇨🇿 Slava Dosedel | 3-6 7-6(1) 6-2 | H2H |
| 🇪🇸 Felix Mantilla | d. | 🇦🇷 Guillermo Canas | 7-6(9) 6-3 | H2H |
| 🇸🇪 Jonas Bjorkman | d. | 🇸🇰 Jan Kroslak | 6-2 7-6(4) | H2H |
| 🇵🇭 Cecil Mamiit | d. | Juan Antonio Marin | 7-6(1) 6-4 | H2H |
| 🇬🇷 Solon Peppas | d. | 🇪🇸 Alberto Martin | 5-7 6-3 6-4 | H2H |
| 🇬🇧 Greg Rusedski | d. | 🇩🇰 Kenneth Carlsen | 6-7(3) 6-2 7-5 | H2H |