ATP 250 · 1999-05-03 · draw of 32
Delray Beach 1999
ClayFinal
| 🇦🇺 Lleyton Hewitt | d. | 🇧🇪 Xavier Malisse | 6-4 6-7(2) 6-1 | H2H |
Semifinals
| 🇦🇺 Lleyton Hewitt | d. | 🇫🇷 Sebastien Grosjean | 6-3 6-2 | H2H |
| 🇧🇪 Xavier Malisse | d. | 🇦🇺 Scott Draper | 6-4 6-4 | H2H |
Quarterfinals
| 🇫🇷 Sebastien Grosjean | d. | 🇵🇭 Cecil Mamiit | 6-2 6-1 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇲 Sargis Sargsian | 6-3 6-1 | H2H |
| 🇦🇺 Scott Draper | d. | 🇸🇪 Magnus Larsson | 4-6 6-3 6-3 | H2H |
| 🇧🇪 Xavier Malisse | d. | 🇦🇷 Hernan Gumy | 7-5 6-4 | H2H |
Round of 16
| 🇫🇷 Sebastien Grosjean | d. | 🇧🇪 Christophe Rochus | 6-1 6-4 | H2H |
| 🇵🇭 Cecil Mamiit | d. | 🇦🇺 Sandon Stolle | 6-4 6-2 | H2H |
| 🇦🇲 Sargis Sargsian | d. | 🇸🇪 Magnus Norman | 6-2 6-0 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇹 Stefan Koubek | 2-6 6-3 6-4 | H2H |
| 🇸🇪 Magnus Larsson | d. | 🇺🇸 Geoff Grant | 6-7(4) 6-2 6-3 | H2H |
| 🇦🇺 Scott Draper | d. | 🇧🇾 Max Mirnyi | 6-4 6-7(4) 6-4 | H2H |
| 🇦🇷 Hernan Gumy | d. | 🇺🇸 Justin Gimelstob | 7-6(2) 7-6(2) | H2H |
| 🇧🇪 Xavier Malisse | d. | 🇸🇪 Mikael Tillstrom | 7-5 6-4 | H2H |
Round of 32
| 🇫🇷 Sebastien Grosjean | d. | 🇪🇸 Alex Calatrava | 7-6(5) 6-7(2) 3-0 RET | H2H |
| 🇧🇪 Christophe Rochus | d. | 🇫🇷 Guillaume Raoux | 6-3 6-1 | H2H |
| 🇦🇺 Sandon Stolle | d. | 🇦🇷 Martin Rodriguez | 7-6(7) 6-3 | H2H |
| 🇵🇭 Cecil Mamiit | d. | 🇦🇺 Mark Woodforde | 7-6(4) 7-5 | H2H |
| 🇸🇪 Magnus Norman | d. | 🇦🇷 Lucas Arnold Ker | 6-4 6-3 | H2H |
| 🇦🇲 Sargis Sargsian | d. | 🇦🇺 Todd Woodbridge | 6-1 6-1 | H2H |
| 🇦🇹 Stefan Koubek | d. | 🇪🇸 Galo Blanco | 6-4 6-3 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇷 Guillermo Canas | 6-7(12) 6-2 6-4 | H2H |
| 🇸🇪 Magnus Larsson | d. | 🇪🇸 Alberto Martin | 7-5 6-3 | H2H |
| 🇺🇸 Geoff Grant | d. | 🇺🇸 Brian MacPhie | 6-4 6-0 | H2H |
| 🇧🇾 Max Mirnyi | d. | 🇺🇸 Jim Courier | 4-6 6-2 7-6(6) | H2H |
| 🇦🇺 Scott Draper | d. | Juan Antonio Marin | 6-4 7-5 | H2H |
| 🇺🇸 Justin Gimelstob | d. | 🇨🇿 Petr Korda | 6-4 6-2 | H2H |
| 🇦🇷 Hernan Gumy | d. | 🇨🇦 Sebastien Lareau | 6-3 6-2 | H2H |
| 🇧🇪 Xavier Malisse | d. | 🇺🇸 Paul Goldstein | 7-6(4) 6-1 | H2H |
| 🇸🇪 Mikael Tillstrom | d. | 🇺🇸 Vincent Spadea | 7-5 0-6 6-4 | H2H |