ATP 500 · 1999-08-16 · draw of 56
Indianapolis 1999
HardFinal
| 🇪🇨 Nicolas Lapentti | d. | 🇺🇸 Vincent Spadea | 4-6 6-4 6-4 | H2H |
Semifinals
| 🇪🇨 Nicolas Lapentti | d. | 🇳🇱 Jan Siemerink | 6-4 6-2 | H2H |
| 🇺🇸 Vincent Spadea | d. | 🇫🇷 Sebastien Grosjean | 6-3 6-7(4) 7-6(4) | H2H |
Quarterfinals
| 🇳🇱 Jan Siemerink | d. | 🇦🇺 Patrick Rafter | W/O | H2H |
| 🇪🇨 Nicolas Lapentti | d. | 🇪🇸 Carlos Moya | 6-1 6-2 | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇧🇷 Gustavo Kuerten | 6-4 6-3 | H2H |
| 🇺🇸 Vincent Spadea | d. | 🇺🇸 Pete Sampras | 6-4 3-6 RET | H2H |
Round of 16
| 🇦🇺 Patrick Rafter | d. | 🇨🇦 Daniel Nestor | 7-6(5) 6-2 | H2H |
| 🇳🇱 Jan Siemerink | d. | 🇸🇪 Magnus Larsson | 6-2 6-3 | H2H |
| 🇪🇸 Carlos Moya | d. | 🇫🇷 Cedric Pioline | 6-4 6-2 | H2H |
| 🇪🇨 Nicolas Lapentti | d. | 🇫🇷 Arnaud Di Pasquale | 6-4 7-6(5) | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇨🇱 Marcelo Rios | 6-4 6-2 | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇸🇪 Magnus Norman | 6-4 7-5 | H2H |
| 🇺🇸 Vincent Spadea | d. | 🇫🇷 Arnaud Clement | 7-5 7-6(5) | H2H |
| 🇺🇸 Pete Sampras | d. | 🇧🇾 Max Mirnyi | 7-6(4) 6-3 | H2H |
Round of 32
| 🇦🇺 Patrick Rafter | d. | 🇫🇷 Antony Dupuis | 2-6 6-2 7-6(1) | H2H |
| 🇨🇦 Daniel Nestor | d. | 🇩🇪 David Prinosil | 6-3 6-3 | H2H |
| 🇸🇪 Magnus Larsson | d. | 🇸🇪 Thomas Enqvist | 7-6(6) 6-4 | H2H |
| 🇳🇱 Jan Siemerink | d. | 🇩🇪 Tommy Haas | 6-3 7-5 | H2H |
| 🇪🇸 Carlos Moya | d. | 🇨🇿 Daniel Vacek | 1-6 6-4 7-6(6) | H2H |
| 🇫🇷 Cedric Pioline | d. | 🇪🇸 Alberto Martin | 6-0 6-3 | H2H |
| 🇪🇨 Nicolas Lapentti | d. | 🇺🇸 Jared Palmer | 6-2 6-2 | H2H |
| 🇫🇷 Arnaud Di Pasquale | d. | 🇦🇺 Mark Philippoussis | 6-3 3-6 6-1 | H2H |
| 🇨🇱 Marcelo Rios | d. | 🇮🇱 Harel Levy | 6-2 7-6(5) | H2H |
| 🇫🇷 Sebastien Grosjean | d. | 🇪🇸 Albert Costa | 6-7(0) 6-2 7-5 | H2H |
| 🇸🇪 Magnus Norman | d. | 🇷🇴 Andrei Pavel | 6-3 6-1 | H2H |
| 🇧🇷 Gustavo Kuerten | d. | 🇳🇱 Sjeng Schalken | 6-4 6-2 | H2H |
| 🇫🇷 Arnaud Clement | d. | 🇸🇪 Thomas Johansson | 6-3 6-2 | H2H |
| 🇺🇸 Vincent Spadea | d. | 🇩🇪 Axel Pretzsch | 6-3 6-4 | H2H |
| 🇧🇾 Max Mirnyi | d. | 🇿🇦 Wayne Ferreira | 7-5 6-4 | H2H |
| 🇺🇸 Pete Sampras | d. | 🇫🇷 Guillaume Raoux | 6-4 7-5 | H2H |