# 1999 Great American Insurance ATP Championships – Singles

Pete Sampras defeated the defending champion Patrick Rafter in a rematch of the previous year's final, 7–6$^{(9–7)}$, 6–3 to win the singles tennis title at the 1999 Cincinnati Masters.
With the win, Sampras reached his fourth title in this season, after previously winning at London (Queen's), Wimbledon and Los Angeles.

## Seeds

The top eight seeds received a bye to the second round.
* Pete Sampras (champion)
* Patrick Rafter (final)
* Andre Agassi (semifinals)
* Yevgeny Kafelnikov (semifinals)
* Tim Henman (quarterfinals)
* Gustavo Kuerten (quarterfinals)
* Richard Krajicek (quarterfinals)
* Álex Corretja (second round)
* Todd Martin (second round)
* Carlos Moyà (first round)
* Tommy Haas (third round)
* Nicolas Kiefer (third round)
* Thomas Enqvist (second round)
* Álbert Costa (second round)
* Nicolás Lapentti (third round)
* Thomas Johansson (first round, retired)

## 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

| Semifinals | Semifinals | Semifinals | Semifinals | Final | Final | Final | Final |
| 1 | Pete Sampras | 7$^9$ | 6 | | | | |
| 3 | Andre Agassi | 6$^7$ | 4 | | | | |
| 3 | Andre Agassi | 6$^7$ | 4 | 1 | Pete Sampras | 7$^9$ | 6 |
| | | | | 2 | Patrick Rafter | 6$^7$ | 3 |
| 4 | Yevgeny Kafelnikov | 4 | 2 | 2 | Patrick Rafter | 6$^7$ | 3 |
| 2 | Patrick Rafter | 6 | 6 | | | | |

### Top half
#### Section 1

| 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 | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 1 | P Sampras | 7$^{11}$ | 6 | | | | | | | | |
| | J Siemerink | 6 | 6 | | | J Siemerink | 6$^9$ | 4 | | | | | | | | |
| | J Krošlák | 1 | 2 | | | | | | 1 | P Sampras | 7 | 7$^7$ | | | | |
| | M Larsson | 7$^7$ | 6 | | | | | | | R Schüttler | 5 | 6$^2$ | | | | |
| Q | A Clément | 6$^5$ | 0 | | | M Larsson | 5 | 6$^5$ | | | | | | | | |
| | R Schüttler | 6 | 3 | | | R Schüttler | 7 | 7$^7$ | | | | | | | | |
| 16 | T Johansson | 4 | 4$^r$ | | | | | | | | | | 1 | P Sampras | 6 | 6 |
| 9 | T Martin | 6 | 5 | 6 | | | | | | | | | 7 | R Krajicek | 4 | 2 |
| Q | R Delgado | 4 | 7 | 2 | 9 | T Martin | 4 | 4 | | | | | | | | |
| | J Gimelstob | 6 | 6 | | | J Gimelstob | 6 | 6 | | | | | | | | |
| | J Stoltenberg | 2 | 3 | | | | | | | J Gimelstob | 4 | 2 | | | | |
| WC | R Reneberg | 6$^2$ | 4 | | | | | | 7 | R Krajicek | 6 | 6 | | | | |
| Q | I Ljubičić | 7$^7$ | 6 | | Q | I Ljubičić | 1 | 3 | | | | | | | | |
| | | | | | 7 | R Krajicek | 6 | 6 | | | | | | | | |

#### 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 | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 3 | A Agassi | 6 | 6 | | | | | | | | | |
| | A Di Pasquale | 6 | 6 | | | A Di Pasquale | 4 | 1 | | | | | | | | | |
| WC | M Washington | 4 | 3 | | | | | | | 3 | A Agassi | 7$^7$ | 7$^7$ | | | | |
| Q | A Pretzsch | 7$^7$ | 5 | 3 | | | | | | | J Novák | 6$^3$ | 6$^5$ | | | | |
| | J Novák | 6$^3$ | 7 | 6 | | J Novák | 7$^7$ | 7$^8$ | | | | | | | | | |
| | A Ilie | 4 | 6 | 2 | 14 | Á Costa | 6$^3$ | 6$^6$ | | | | | | | | | |
| 14 | Á Costa | 6 | 3 | 6 | | | | | | | | | | 3 | A Agassi | 6 | 7$^{12}$ |
| 11 | T Haas | 7 | 6 | | | | | | | | | | | 6 | G Kuerten | 2 | 6$^{10}$ |
| WC | X Malisse | 5 | 2 | | 11 | T Haas | 6 | 6$^1$ | 6 | | | | | | | | |
| | B Black | 6$^5$ | 3 | | | F Santoro | 0 | 7$^7$ | 3 | | | | | | | | |
| | F Santoro | 7$^7$ | 6 | | | | | | | 11 | T Haas | 5 | 5 | | | | |
| | A Martín | 7$^7$ | 6 | | | | | | | 6 | G Kuerten | 7 | 7 | | | | |
| | D Prinosil | 6$^3$ | 3 | | | A Martín | 2 | 3 | | | | | | | | | |
| | | | | | 6 | G Kuerten | 6 | 6 | | | | | | | | | |

### Bottom half
#### 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 | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | 5 | T Henman | 6 | 6 | | | | | | | | | |
| | J van Lottum | 6 | 6 | | J van Lottum | 2 | 1 | | | | | | | | | |
| Q | W Black | 3 | 2 | | | | | | 5 | T Henman | 6 | 6 | | | | |
| WC | P Goldstein | 6 | 6 | | | | | | 12 | N Kiefer | 4 | 1 | | | | |
| Q | M Woodforde | 3 | 2 | WC | P Goldstein | 6 | 4 | 6$^{10}$ | | | | | | | | |
| | S Grosjean | 5 | 3 | 12 | N Kiefer | 2 | 6 | 7$^{12}$ | | | | | | | | |
| 12 | N Kiefer | 7 | 6 | | | | | | | | | | 5 | T Henman | 5 | 5 |
| 13 | T Enqvist | 7 | 7$^7$ | | | | | | | | | | 4 | Y Kafelnikov | 7 | 7 |
| Q | W Arthurs | 5 | 6$^1$ | 13 | T Enqvist | 1 | 5 | | | | | | | | | |
| | W Ferreira | 3 | 4 | | C Woodruff | 6 | 7 | | | | | | | | | |
| | C Woodruff | 6 | 6 | | | | | | | C Woodruff | 4 | 4 | | | | |
| | A Pavel | 4 | 5 | | | | | | 4 | Y Kafelnikov | 6 | 6 | | | | |
| | J Björkman | 6 | 7 | | J Björkman | 1 | 4 | | | | | | | | | |
| | | | | 4 | Y Kafelnikov | 6 | 6 | | | | | | | | | |

#### Section 4

| 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 | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals |
| | | | | | 8 | Á Corretja | 3 | 7$^7$ | 2 | | | | | | | | |
| | M Chang | 6 | 6 | | | M Chang | 6 | 6$^5$ | 6 | | | | | | | | |
| | M Safin | 3 | 4 | | | | | | | | M Chang | 6 | 6 | | | | |
| | G Ivanišević | 6$^1$ | 2 | | | | | | | | C Pioline | 1 | 4 | | | | |
| | J Courier | 7$^7$ | 6 | | | J Courier | 7$^7$ | 6$^4$ | 0$^r$ | | | | | | | | |
| | C Pioline | 6 | 6 | | | C Pioline | 6$^5$ | 7$^7$ | 2 | | | | | | | | |
| 10 | C Moyà | 4 | 1 | | | | | | | | | | | | M Chang | 2 | 1 |
| 15 | N Lapentti | 6 | 6 | | | | | | | | | | | 2 | P Rafter | 6 | 6 |
| | V Spadea | 2 | 2 | | 15 | N Lapentti | 6 | 7$^7$ | | | | | | | | | |
| | S Schalken | 6 | 3 | 4 | | J-M Gambill | 0 | 6$^3$ | | | | | | | | | |
| | J-M Gambill | 4 | 6 | 6 | | | | | | 15 | N Lapentti | 2 | 3 | | | | |
| WC | C Mamiit | 4 | 4 | | | | | | | 2 | P Rafter | 6 | 6 | | | | |
| | D Vacek | 6 | 6 | | | D Vacek | 6$^3$ | 3 | | | | | | | | | |
| | | | | | 2 | P Rafter | 7$^7$ | 6 | | | | | | | | | |

## Qualifying
### Qualifying seeds

* Arnaud Clément (qualified)
* Mark Woodforde (qualified)
* Ramón Delgado (qualified)
* Bernd Karbacher (qualifying competition)
* Wayne Arthurs (qualified)
* Martin Damm (qualifying competition)
* Ivan Ljubičić (qualified)
* Wayne Black (qualified)
* Sébastien Lareau (qualifying competition)
* Max Mirnyi (qualifying competition)
* Axel Pretzsch (qualified)
* Mosé Navarra (qualifying competition)
* Todd Woodbridge (first round)
* Alex O'Brien (qualifying competition)

### Qualifiers

* Arnaud Clément
* Mark Woodforde
* Ramón Delgado
* Axel Pretzsch
* Wayne Arthurs
* Wayne Black
* Ivan Ljubičić

### Qualifying draw
#### First qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 1 | Arnaud Clément | 6 | 6 | | | | | |
| WC | Jeff Morrison | 1 | 2 | | | | | |
| WC | Jeff Morrison | 1 | 2 | 1 | Arnaud Clément | 6 | 2 | 7 |
| | | | | 14 | Alex O'Brien | 2 | 6 | 5 |
| | Cristiano Caratti | 0 | 3 | 14 | Alex O'Brien | 2 | 6 | 5 |
| 14 | Alex O'Brien | 6 | 6 | | | | | |

#### Second qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 2 | Mark Woodforde | 6 | 6 | | | | |
| | Bob Bryan | 4 | 2 | | | | |
| | Bob Bryan | 4 | 2 | 2 | Mark Woodforde | 6 | 6 |
| | | | | 12 | Mosé Navarra | 0 | 3 |
| | Michael Tebbutt | 3 | 1 | 12 | Mosé Navarra | 0 | 3 |
| 12 | Mosé Navarra | 6 | 6 | | | | |

#### Third qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 3 | Ramón Delgado | 6 | 2 | 6 | | | | |
| | Barry Cowan | 2 | 6 | 1 | | | | |
| | Barry Cowan | 2 | 6 | 1 | 3 | Ramón Delgado | 6 | 6 |
| | | | | | | Michael Joyce | 3 | 2 |
| | Michael Joyce | 6 | 4 | 7 | | Michael Joyce | 3 | 2 |
| 13 | Todd Woodbridge | 3 | 6 | 6 | | | | |

#### Fourth qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 4 | Bernd Karbacher | 6 | 6 | | | | | |
| WC | Mike Bryan | 2 | 2 | | | | | |
| WC | Mike Bryan | 2 | 2 | | 4 | Bernd Karbacher | 4 | 5 |
| | | | | | 11 | Axel Pretzsch | 6 | 7 |
| WC | Wynn Criswell | 6 | 3 | 2 | 11 | Axel Pretzsch | 6 | 7 |
| 11 | Axel Pretzsch | 3 | 6 | 6 | | | | |

#### Fifth qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 5 | Wayne Arthurs | 4 | 6 | 7 | | | | |
| | Michael Hill | 6 | 3 | 6 | | | | |
| | Michael Hill | 6 | 3 | 6 | 5 | Wayne Arthurs | 6 | 6 |
| | | | | | 10 | Max Mirnyi | 3 | 4 |
| WC | Marq Foster | 3 | 2 | | 10 | Max Mirnyi | 3 | 4 |
| 10 | Max Mirnyi | 6 | 6 | | | | | |

#### Sixth qualifier

| First round | First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 6 | Martin Damm | 4 | 6 | 6 | | | | |
| | Mark Knowles | 6 | 1 | 4 | | | | |
| | Mark Knowles | 6 | 1 | 4 | 6 | Martin Damm | 3 | 2 |
| | | | | | 8 | Wayne Black | 6 | 6 |
| | Kevin Ullyett | 0 | 4 | | 8 | Wayne Black | 6 | 6 |
| 8 | Wayne Black | 6 | 6 | | | | | |

#### Seventh qualifier

| First round | First round | First round | First round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| 7 | Ivan Ljubičić | 7 | 6 | | | | |
| | Jared Palmer | 6 | 4 | | | | |
| | Jared Palmer | 6 | 4 | 7 | Ivan Ljubičić | 6 | 7 |
| | | | | 9 | Sébastien Lareau | 1 | 6 |
| | Jonathan Stark | 3 | 3 | 9 | Sébastien Lareau | 1 | 6 |
| 9 | Sébastien Lareau | 6 | 6 | | | | |