ATP 250 · 1999-04-19 · draw of 32
Orlando 1999
ClayFinal
| 🇸🇪 Magnus Norman | d. | 🇦🇷 Guillermo Canas | 6-0 6-3 | H2H |
Semifinals
| 🇸🇪 Magnus Norman | d. | 🇧🇾 Max Mirnyi | 6-2 6-1 | H2H |
| 🇦🇷 Guillermo Canas | d. | 🇳🇴 Christian Ruud | 5-2 RET | H2H |
Quarterfinals
| 🇸🇪 Magnus Norman | d. | 🇷🇴 Gabriel Trifu | 7-5 6-2 | H2H |
| 🇧🇾 Max Mirnyi | d. | 🇺🇸 Jim Courier | 6-3 6-7(3) 6-4 | H2H |
| 🇦🇷 Guillermo Canas | d. | 🇪🇸 Alberto Martin | 6-4 7-6(4) | H2H |
| 🇳🇴 Christian Ruud | d. | 🇦🇷 Hernan Gumy | 7-6(10) 6-4 | H2H |
Round of 16
| 🇷🇴 Gabriel Trifu | d. | 🇦🇲 Sargis Sargsian | 6-4 6-4 | H2H |
| 🇸🇪 Magnus Norman | d. | 🇪🇸 Carlos Costa | 6-4 6-4 | H2H |
| 🇧🇾 Max Mirnyi | d. | 🇫🇷 Rodolphe Cadart | 6-2 7-6(7) | H2H |
| 🇺🇸 Jim Courier | d. | 🇪🇸 Galo Blanco | 7-5 6-4 | H2H |
| 🇦🇷 Guillermo Canas | d. | 🇦🇺 Lleyton Hewitt | 6-3 6-3 | H2H |
| 🇪🇸 Alberto Martin | d. | 🇮🇹 Gianluca Pozzi | 6-3 3-6 6-2 | H2H |
| 🇳🇴 Christian Ruud | d. | 🇦🇷 Lucas Arnold Ker | 3-6 7-6(3) 6-2 | H2H |
| 🇦🇷 Hernan Gumy | d. | 🇦🇺 Jason Stoltenberg | 7-6(3) 7-6(4) | H2H |
Round of 32
| 🇦🇲 Sargis Sargsian | d. | 🇺🇸 Jan-Michael Gambill | 3-6 6-3 7-6(4) | H2H |
| 🇷🇴 Gabriel Trifu | d. | 🇺🇸 Chris Woodruff | 7-6(3) 6-0 | H2H |
| 🇪🇸 Carlos Costa | d. | 🇮🇹 Laurence Tieleman | 6-3 6-0 | H2H |
| 🇸🇪 Magnus Norman | d. | 🇫🇷 Olivier Malcor | 6-3 6-0 | H2H |
| 🇧🇾 Max Mirnyi | d. | 🇦🇺 Scott Draper | 6-4 3-6 6-3 | H2H |
| 🇫🇷 Rodolphe Cadart | d. | 🇨🇿 Petr Korda | 4-6 7-6(4) 6-1 | H2H |
| 🇪🇸 Galo Blanco | d. | 🇺🇸 Alex O'Brien | 7-5 6-3 | H2H |
| 🇺🇸 Jim Courier | d. | 🇸🇪 Mikael Tillstrom | 6-4 7-5 | H2H |
| 🇦🇺 Lleyton Hewitt | d. | 🇦🇷 Martin Rodriguez | 6-3 6-4 | H2H |
| 🇦🇷 Guillermo Canas | d. | 🇦🇹 Stefan Koubek | 6-4 7-6(3) | H2H |
| 🇪🇸 Alberto Martin | d. | 🇧🇪 Johan Van Herck | 6-3 3-6 7-5 | H2H |
| 🇮🇹 Gianluca Pozzi | d. | 🇸🇪 Magnus Larsson | 3-6 6-3 6-4 | H2H |
| 🇳🇴 Christian Ruud | d. | 🇪🇸 Alex Calatrava | 6-4 6-2 | H2H |
| 🇦🇷 Lucas Arnold Ker | d. | 🇧🇬 Orlin Stanoytchev | 5-7 6-0 6-4 | H2H |
| 🇦🇷 Hernan Gumy | d. | 🇦🇺 Todd Woodbridge | 6-3 6-7(2) 6-4 | H2H |
| 🇦🇺 Jason Stoltenberg | d. | 🇺🇸 Justin Gimelstob | 6-0 6-7(5) 6-4 | H2H |