| WON | LOST | |
| Carpet | 6 | 2 |
| Clay | 1 | 4 |
| Grass | 12 | 5 |
| Hard | 27 | 14 |
| WON | LOST | |
| Finals | 1 | 3 |
| Semifinals | 4 | 2 |
| Quarterfinals | 6 | 3 |
| Q8 | 9 | 2 |
| Q16 | 11 | 4 |
| Q32 | 5 | 3 |
| Q64 | 4 | 1 |
| WON | LOST | |
| Adelaide, Australia | 4 | 1 |
| Sydney, Australia | 2 | 1 |
| Australian Open, Australia | 1 | 1 |
| Scottsdale, United States | 4 | 1 |
| Indian Wells, United States | 1 | 1 |
| Key Biscayne, United States | 1 | 1 |
| Orlando, United States | 1 | 1 |
| Atlanta, United States | 1 | |
| Delray Beach, United States | 5 | |
| Roland Garros, France | 1 | |
| London / Queen's Club, England | 4 | 1 |
| Nottingham, England | 2 | 1 |
| Wimbledon, England | 2 | 1 |
| Los Angeles, United States | 2 | 1 |
| US Open, United States | 2 | 1 |
| Singapore, Singapore | 3 | 1 |
| Lyon, France | 4 | 1 |
| Stuttgart Indoor, Germany | 1 | |
| Paris Indoor, France | 2 | 1 |
| WON | LOST | |
| Alex O'brien | 1 | |
| Andre Agassi | 1 | |
| Andrei Medvedev | 1 | |
| Arnaud Clement | 1 | |
| Axel Pretzsch | 1 | |
| Boris Becker | 1 | |
| Cedric Pioline | 2 | 1 |
| Chris Wilkinson | 1 | |
| Chris Woodruff | 1 | |
| Diego Nargiso | 1 | |
| Fernando Meligeni | 1 | |
| Greg Rusedski | 1 | |
| Guillermo Canas | 2 | 1 |
| Jan-Michael Gambill | 1 | |
| Jason Stoltenberg | 1 | |
| Jerome Golmard | 1 | |
| Jiri Novak | 1 | |
| John Van lottum | 1 | |
| Karim Alami | 1 | |
| Karol Kucera | 1 | |
| Kenneth Carlsen | 1 | |
| Magnus Norman | 1 | |
| Marat Safin | 1 | |
| Marc Rosset | 1 | |
| Marcelo Filippini | 1 | |
| Marcelo Rios | 1 | |
| Mark Philippoussis | 1 | 1 |
| Mark Woodforde | 3 | 1 |
| Martin Rodriguez | 1 | 1 |
| Mikael Tillstrom | 1 | |
| Nicolas Kiefer | 2 | |
| Nicolas Lapentti | 1 | |
| Patrick Rafter | 2 | |
| Paul Goldstein | 1 | |
| Pete Sampras | 1 | |
| Roger Federer | 1 | |
| Sargis Sargsian | 1 | |
| Sebastien Grosjean | 1 | |
| Slava Dosedel | 1 | |
| Stefan Koubek | 1 | |
| Thomas Enqvist | 1 | |
| Todd Martin | 1 | |
| Tommy Haas | 1 | |
| Vincent Spadea | 1 | |
| Wayne Arthurs | 1 | |
| Xavier Malisse | 1 | |
| Yevgeny Kafelnikov | 1 |
Lleyton Hewitt tennis results in year 1999 tennis statistics
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