ATP 500 · 1999-08-16 · draw of 56
Washington 1999
HardFinal
| 🇺🇸 Andre Agassi | d. | 🇷🇺 Yevgeny Kafelnikov | 7-6(3) 6-1 | H2H |
Semifinals
| 🇺🇸 Andre Agassi | d. | 🇺🇸 Todd Martin | 6-4 6-2 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇩🇪 Nicolas Kiefer | 6-2 2-6 6-3 | H2H |
Quarterfinals
| 🇺🇸 Andre Agassi | d. | 🇫🇷 Fabrice Santoro | 6-4 7-5 | H2H |
| 🇺🇸 Todd Martin | d. | 🇺🇸 Paul Goldstein | 6-4 7-5 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇸🇰 Jan Kroslak | 6-4 6-3 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇨🇿 Tomas Zib | 6-1 6-7(7) 7-5 | H2H |
Round of 16
| 🇺🇸 Andre Agassi | d. | 🇩🇪 Bjorn Phau | 6-1 6-3 | H2H |
| 🇫🇷 Fabrice Santoro | d. | 🇷🇺 Marat Safin | 6-0 6-4 | H2H |
| 🇺🇸 Todd Martin | d. | 🇵🇾 Ramon Delgado | W/O | H2H |
| 🇺🇸 Paul Goldstein | d. | 🇪🇸 Alex Corretja | 7-6(9) 7-6(5) | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇳🇱 John van Lottum | 7-5 6-2 | H2H |
| 🇸🇰 Jan Kroslak | d. | 🇬🇧 Tim Henman | 3-6 6-3 6-4 | H2H |
| 🇨🇿 Tomas Zib | d. | 🇨🇭 Marc Rosset | 6-3 6-2 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇺🇸 Justin Gimelstob | 7-5 6-4 | H2H |
Round of 32
| 🇺🇸 Andre Agassi | d. | 🇸🇪 Mikael Tillstrom | 6-1 6-1 | H2H |
| 🇩🇪 Bjorn Phau | d. | 🇮🇹 Laurence Tieleman | 3-6 6-3 6-4 | H2H |
| 🇫🇷 Fabrice Santoro | d. | Ronald Agenor | 6-4 6-4 | H2H |
| 🇷🇺 Marat Safin | d. | 🇨🇦 Sebastien Lareau | 7-5 7-6(2) | H2H |
| 🇺🇸 Todd Martin | d. | 🇩🇰 Kristian Pless | 6-4 6-4 | H2H |
| 🇵🇾 Ramon Delgado | d. | 🇺🇸 Michael Chang | 6-4 1-6 6-3 | H2H |
| 🇺🇸 Paul Goldstein | d. | 🇨🇿 Martin Damm | 5-7 7-5 6-2 | H2H |
| 🇪🇸 Alex Corretja | d. | 🇮🇹 Gianluca Pozzi | 7-6(5) 1-6 7-5 | H2H |
| 🇩🇪 Nicolas Kiefer | d. | 🇺🇸 Mashiska Washington | 6-4 6-2 | H2H |
| 🇳🇱 John van Lottum | d. | 🇩🇰 Kenneth Carlsen | 6-4 1-6 7-6(5) | H2H |
| 🇸🇰 Jan Kroslak | d. | 🇨🇭 Lorenzo Manta | 7-5 7-6(3) | H2H |
| 🇬🇧 Tim Henman | d. | 🇳🇱 Peter Wessels | 7-6(2) 7-5 | H2H |
| 🇨🇭 Marc Rosset | d. | 🇨🇱 Fernando Gonzalez | 7-6(9) 6-4 | H2H |
| 🇨🇿 Tomas Zib | d. | 🇩🇪 Rainer Schuettler | 6-7(2) 7-5 3-0 RET | H2H |
| 🇺🇸 Justin Gimelstob | d. | 🇦🇺 Wayne Arthurs | 6-4 6-1 | H2H |
| 🇷🇺 Yevgeny Kafelnikov | d. | 🇿🇼 Wayne Black | 0-6 6-2 6-4 | H2H |