# 1999 Lipton Championships – Men's singles

Richard Krajicek defeated Sébastien Grosjean in the final, 4–6, 6–1, 6–2, 7–5 to win the men's singles tennis title at the 1999 Miami Open.
Marcelo Ríos was the defending champion, but lost in the fourth round to Dominik Hrbatý.

## Seeds

All thirty-two seeds received a bye to the second round.
* Carlos Moyà (fourth round)
* Pete Sampras (quarterfinals)
* Yevgeny Kafelnikov (second round)
* Álex Corretja (fourth round)
* Patrick Rafter (third round)
* Tim Henman (third round)
* Richard Krajicek (champion)
* Marcelo Ríos (fourth round)
* Andre Agassi (second round)
* Mark Philippoussis (third round)
* Karol Kučera (fourth round)
* Greg Rusedski (fourth round)
* Goran Ivanišević (second round)
* Thomas Enqvist (semifinals)
* Álbert Costa (fourth round)
* Gustavo Kuerten (second round)
* Thomas Johansson (second round)
* Tommy Haas (second round)
* Félix Mantilla (third round)
* Francisco Clavet (semifinals)
* Wayne Ferreira (second round)
* Marc Rosset (second round)
* Marat Safin (fourth round)
* Alberto Berasategui (second round, retired)
* Byron Black (third round)
* Jan Siemerink (third round)
* Nicolas Kiefer (quarterfinals)
* Jérôme Golmard (quarterfinals)
* Fabrice Santoro (third round)
* Bohdan Ulihrach (second round)
* Jonas Björkman (third round)
* Jason Stoltenberg (third round)

## Draw
### Key

* Q = Qualifier
* WC = Wild card
* LL = Lucky loser
* Alt = Alternate
* SE = Special exempt
* PR = Protected ranking
* ITF = ITF entry
* JE = Junior exempt
* w/o = Walkover
* r = Retired
* d = Defaulted
* SR = Special ranking

### Finals

| Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final | Final | Final | Final | |
| | Sébastien Grosjean | 6 | 5 | 6 | | | | | | | | | | | | | |
| | Dominik Hrbatý | 3 | 7 | 1 | | | | | | | | | | | | | |
| | Dominik Hrbatý | 3 | 7 | 1 | | Sébastien Grosjean | 3 | 6 | 6 | | | | | | | | |
| | | | | | 20 | Francisco Clavet | 6 | 3 | 1 | | | | | | | | |
| 20 | Francisco Clavet | 7 | 6 | | 20 | Francisco Clavet | 6 | 3 | 1 | | | | | | | | |
| 27 | Nicolas Kiefer | 5 | 3 | | | | | | | | | | | | | | |
| 27 | Nicolas Kiefer | 5 | 3 | | | | | | | | Sébastien Grosjean | 6 | 1 | 2 | 5 | | |
| | | | | | | | | | | 7 | Richard Krajicek | 4 | 6 | 6 | 7 | | |
| 28 | Jérôme Golmard | 3 | 5 | | | | | | | | | | | | | 7 | Richard Krajicek | 4 | 6 | 6 | 7 |
| 14 | Thomas Enqvist | 6 | 7 | | | | | | | | | | | | | | |
| 14 | Thomas Enqvist | 6 | 7 | | 14 | Thomas Enqvist | 4 | 2 | | | | | | | | | |
| | | | | | 7 | Richard Krajicek | 6 | 6 | | | | | | | | | |
| 7 | Richard Krajicek | 6 | 7$^8$ | | 7 | Richard Krajicek | 6 | 6 | | | | | | | | | |
| 2 | Pete Sampras | 2 | 6$^6$ | | | | | | | | | | | | | | |

### Top half
#### Section 1

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | | 1 | C Moyà | 6 | 4 | 6 | | | | | | | | | | |
| | D Sanguinetti | 6 | 6 | | | D Sanguinetti | 3 | 6 | 1 | | | | | | | | | | |
| | G Raoux | 2 | 2 | | | | | | | 1 | C Moyà | 6$^5$ | 6 | 7 | | | | | |
| | D Prinosil | 6 | 6$^7$ | 4 | | | | | | 32 | J Stoltenberg | 7$^7$ | 1 | 5 | | | | | |
| | W Black | 1 | 7$^9$ | 6 | | W Black | 4 | 6 | 6$^2$ | | | | | | | | | | |
| | | | | | 32 | J Stoltenberg | 6 | 1 | 7$^7$ | | | | | | | | | | |
| | | | | | | | | | | | | | | | 1 | C Moyà | 6 | 4 | 6$^9$ |
| | | | | | | | | | | | | | | | | S Grosjean | 3 | 6 | 7$^{11}$ |
| | | | | | 17 | T Johansson | 6$^6$ | 6 | 3 | | | | | | | | | | |
| Q | R Agénor | 4 | 4 | | | J Krošlák | 7$^8$ | 2 | 6 | | | | | | | | | | |
| | J Krošlák | 6 | 6 | | | | | | | | J Krošlák | 2 | 4 | | | | | | |
| | S Grosjean | 6 | 7 | | | | | | | | S Grosjean | 6 | 6 | | | | | | |
| | L Tieleman | 1 | 5 | | | S Grosjean | 6 | 7$^7$ | | | | | | | | | | | |
| | | | | | 16 | G Kuerten | 3 | 6$^4$ | | | | | | | | | | | |

#### Section 2

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | | 9 | A Agassi | 6 | 3 | 2 | | | | | | | | |
| | D Hrbatý | 6$^5$ | 6 | 6 | | D Hrbatý | 1 | 6 | 6 | | | | | | | | |
| | Y El Aynaoui | 7$^7$ | 3 | 0 | | | | | | | D Hrbatý | 6 | 6 | | | | |
| | J A Marín | 7$^7$ | 7$^9$ | | | | | | | | J A Marín | 2 | 4 | | | | |
| | M Chang | 6$^3$ | 6$^7$ | | | J A Marín | 2 | | | | | | | | | | |
| | | | | | 24 | A Berasategui | 1$^r$ | | | | | | | | | | |
| | | | | | | | | | | | | | | | D Hrbatý | 6 | 6 |
| | | | | | | | | | | | | | | 8 | M Ríos | 2 | 0 |
| | | | | | 25 | B Black | 6 | 6 | | | | | | | | | |
| Q | S Campbell | 5 | 6 | 3 | Q | N Escudé | 4 | 3 | | | | | | | | | |
| Q | N Escudé | 7 | 4 | 6 | | | | | | 25 | B Black | 3 | 4 | | | | |
| | M Puerta | 3 | 6 | 2 | | | | | | 8 | M Ríos | 6 | 6 | | | | |
| | S Draper | 6 | 2 | 6 | | S Draper | 6$^6$ | 3 | | | | | | | | | |
| | | | | | 8 | M Ríos | 7$^8$ | 6 | | | | | | | | | |

#### Section 3

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | 3 | Y Kafelnikov | 7$^8$ | 6$^4$ | 2 | | | | | | | | | |
| | V Spadea | 6 | 6 | | V Spadea | 6$^6$ | 7$^7$ | 6 | | | | | | | | | |
| | F Squillari | 3 | 2 | | | | | | | V Spadea | 6 | 6 | | | | | |
| Q | X Malisse | 5 | 2 | | | | | | 29 | F Santoro | 3 | 2 | | | | | |
| | J-M Gambill | 7 | 6 | | J-M Gambill | 5 | 2 | | | | | | | | | | |
| | | | | 29 | F Santoro | 7 | 6 | | | | | | | | | | |
| | | | | | | | | | | | | | | V Spadea | 5 | 6 | 4 |
| | | | | | | | | | | | | | 20 | F Clavet | 7 | 4 | 6 |
| | | | | 20 | F Clavet | 7 | 1 | | | | | | | | | | |
| | C Ruud | 6 | 7$^8$ | | C Ruud | 5 | 0$^r$ | | | | | | | | | | |
| | P Korda | 2 | 6$^6$ | | | | | | 20 | F Clavet | 6 | 6 | | | | | |
| WC | R Federer | 5 | 6$^4$ | | | | | | | K Carlsen | 2 | 4 | | | | | |
| | K Carlsen | 7 | 7$^7$ | | K Carlsen | 6 | 3 | 6 | | | | | | | | | |
| | | | | 13 | G Ivanišević | 2 | 6 | 4 | | | | | | | | | |

#### Section 4

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | | 12 | G Rusedski | 6 | 6 | | | | | | | | | |
| | A Voinea | 6 | 6 | | | A Voinea | 4 | 4 | | | | | | | | | |
| Q | D Caldwell | 0 | 3 | | | | | | 12 | G Rusedski | 6 | 6 | | | | | |
| | H Dreekmann | 6 | 7 | | | | | | | H Dreekmann | 3 | 4 | | | | | |
| Q | R Reneberg | 3 | 5 | | | H Dreekmann | 6 | 6 | | | | | | | | | |
| | | | | | 21 | W Ferreira | 4 | 4 | | | | | | | | | |
| | | | | | | | | | | | | | 12 | G Rusedski | 6 | 5 | 2 |
| | | | | | | | | | | | | | 27 | N Kiefer | 4 | 7 | 6 |
| | | | | | 27 | N Kiefer | 6 | 6 | | | | | | | | | |
| Q | A Clément | 6$^4$ | 6 | 6 | Q | A Clément | 1 | 2 | | | | | | | | | |
| Q | J van Lottum | 7$^7$ | 4 | 4 | | | | | 27 | N Kiefer | 7$^7$ | 6 | | | | | |
| | A Ilie | 6 | 6 | | | | | | 5 | P Rafter | 6$^5$ | 4 | | | | | |
| | G Blanco | 3 | 4 | | | A Ilie | 3 | 5 | | | | | | | | | |
| | | | | | 5 | P Rafter | 6 | 7 | | | | | | | | | |

### Bottom half
#### Section 5

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | | 6 | T Henman | 3 | 6 | 6 | | | | | | | | | |
| WC | C Mamiit | 4 | 6 | 7 | WC | C Mamiit | 6 | 3 | 2 | | | | | | | | | |
| WC | P Goldstein | 6 | 2 | 5 | | | | | | 6 | T Henman | 4 | 6$^7$ | | | | | |
| | M Norman | 6 | 6 | | | | | | | 28 | J Golmard | 6 | 7$^9$ | | | | | |
| | H Arazi | 1 | 1 | | | M Norman | 4 | 3 | | | | | | | | | | |
| | | | | | 28 | J Golmard | 6 | 6 | | | | | | | | | | |
| | | | | | | | | | | | | | | 28 | J Golmard | 4 | 6 | 6 |
| | | | | | | | | | | | | | | 11 | K Kučera | 6 | 2 | 2 |
| | | | | | 22 | M Rosset | 4 | 6 | 6$^6$ | | | | | | | | | |
| | A Pavel | 6 | 6 | | | A Pavel | 6 | 4 | 7$^8$ | | | | | | | | | |
| WC | C Woodruff | 3 | 3 | | | | | | | | A Pavel | 3 | 5 | | | | | |
| | J Tarango | 4 | 5 | | | | | | | 11 | K Kučera | 6 | 7 | | | | | |
| | P Haarhuis | 6 | 7 | | | P Haarhuis | 0 | 2 | | | | | | | | | | |
| | | | | | 11 | K Kučera | 6 | 6 | | | | | | | | | | |

#### Section 6

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | 14 | T Enqvist | 6 | 6 | | | | | | | | | | |
| | S Sargsian | 1 | 1 | WC | B Bryan | 4 | 4 | | | | | | | | | | |
| WC | B Bryan | 6 | 6 | | | | | | 14 | T Enqvist | 4 | 6 | 7$^7$ | | | | |
| | D Vacek | 6 | 6 | | | | | | 19 | F Mantilla | 6 | 3 | 6$^3$ | | | | |
| | M Zabaleta | 4 | 4 | | D Vacek | 2 | 0 | | | | | | | | | | |
| | | | | 19 | F Mantilla | 6 | 6 | | | | | | | | | | |
| | | | | | | | | | | | | | | 14 | T Enqvist | 7 | 6 |
| | | | | | | | | | | | | | | 4 | Á Corretja | 5 | 3 |
| | | | | 30 | B Ulihrach | 6 | 1 | 2 | | | | | | | | | |
| | R Delgado | 7$^7$ | 6 | | R Delgado | 2 | 6 | 6 | | | | | | | | | |
| | R Schüttler | 6$^5$ | 1 | | | | | | | R Delgado | 4 | 6 | 4 | | | | |
| | M Damm | 7$^7$ | 6 | | | | | | 4 | Á Corretja | 6 | 1 | 6 | | | | |
| Q | T Woodbridge | 6$^3$ | 4 | | M Damm | 2 | 2 | | | | | | | | | | |
| | | | | 4 | Á Corretja | 6 | 6 | | | | | | | | | | |

#### Section 7

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | | 7 | R Krajicek | 6 | 4 | 6 | | | | | | | | |
| | J Novák | 2 | 1 | | | S Schalken | 1 | 6 | 1 | | | | | | | | |
| | S Schalken | 6 | 6 | | | | | | | 7 | R Krajicek | 6 | 6 | | | | |
| Q | S Lareau | 5 | 6$^7$ | | | | | | | 26 | J Siemerink | 3 | 2 | | | | |
| Q | A O'Brien | 7 | 7$^9$ | | Q | A O'Brien | 5 | 5 | | | | | | | | | |
| | | | | | 26 | J Siemerink | 7 | 7 | | | | | | | | | |
| | | | | | | | | | | | | | | 7 | R Krajicek | 6 | 6 |
| | | | | | | | | | | | | | | 23 | M Safin | 3 | 1 |
| | | | | | 23 | M Safin | 7 | 6 | | | | | | | | | |
| | B Becker | 6 | 1 | 6 | | B Becker | 5 | 0 | | | | | | | | | |
| | G Pozzi | 4 | 6 | 4 | | | | | | 23 | M Safin | 7$^7$ | 7$^7$ | | | | |
| | M Woodforde | 2 | 1 | | | | | | | 10 | M Philippoussis | 6$^4$ | 6$^3$ | | | | |
| WC | L Hewitt | 6 | 6 | | WC | L Hewitt | 3 | 4 | | | | | | | | | |
| | | | | | 10 | M Philippoussis | 6 | 6 | | | | | | | | | |

#### Section 8

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Third round | Third round | Third round | Third round | Fourth round | Fourth round | Fourth round | Fourth round |
| | | | | 15 | Á Costa | 2 | 6 | 6 | | | | | | | | |
| | A Di Pasquale | 2 | 2 | | S Doseděl | 6 | 3 | 4 | | | | | | | | |
| | S Doseděl | 6 | 6 | | | | | | 15 | Á Costa | 7$^7$ | 6 | | | | |
| | N Lapentti | 6 | 6 | | | | | | | N Lapentti | 6$^3$ | 4 | | | | |
| | M Tillström | 0 | 2 | | N Lapentti | 5 | 7$^7$ | 6 | | | | | | | | |
| | | | | 18 | T Haas | 7 | 6$^3$ | 2 | | | | | | | | |
| | | | | | | | | | | | | | 15 | Á Costa | 4 | 4 |
| | | | | | | | | | | | | | 2 | P Sampras | 6 | 6 |
| | | | | 31 | J Björkman | 1 | 6 | 6 | | | | | | | | |
| | A Medvedev | 6 | 6 | | A Medvedev | 6 | 1 | 2 | | | | | | | | |
| | J Gimelstob | 1 | 0 | | | | | | 31 | J Björkman | 5 | 3 | | | | |
| Q | J F Andersen | 6$^6$ | 2 | | | | | | 2 | P Sampras | 7 | 6 | | | | |
| | J Courier | 7$^8$ | 6 | | J Courier | 3 | 6$^3$ | | | | | | | | | |
| | | | | 2 | P Sampras | 6 | 7$^7$ | | | | | | | | | |