# 1999 Pilot Pen Tennis – Singles

The 1999 Pilot Pen Tennis singles was the singles event of the seventeenth edition of the final tournament in the US Open Series. Steffi Graf was the reigning champion, but had retired after the TIG Classic.
Venus Williams defeated Lindsay Davenport in the final to win her first New Haven title.

## Seeds

* Lindsay Davenport (final)
* Venus Williams (champion)
* Monica Seles (semifinals)
* Jana Novotná (second round)
* Amanda Coetzer (quarterfinals, retired)
* Julie Halard-Decugis (second round)
* Nathalie Tauziat (first round)
* Sandrine Testud (quarterfinals)

## 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 | Semifinals | Final | Final | Final | Final |
| 1 | Lindsay Davenport | 4 | 6 | 6 | | | | |
| | Ruxandra Dragomir | 6 | 2 | 0 | | | | |
| | Ruxandra Dragomir | 6 | 2 | 0 | 1 | Lindsay Davenport | 2 | 5 |
| | | | | | 2 | Venus Williams | 6 | 7 |
| 3 | Monica Seles | 1 | 3 | | 2 | Venus Williams | 6 | 7 |
| 2 | Venus Williams | 6 | 6 | | | | | |

### Top half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals | Semifinals |
| | | | | | 1 | L Davenport | 6 | 6 | | | | | | | | | | |
| | N Dechy | 6 | 6 | | | N Dechy | 4 | 2 | | | | | | | | | | |
| Q | T Panova | 1 | 3 | | | | | | 1 | L Davenport | 6 | 6 | | | | | | |
| Q | K Hrdličková | 4 | 6 | 5 | | | | | | A Mauresmo | 1 | 2 | | | | | | |
| | A Mauresmo | 6 | 3 | 7 | | A Mauresmo | 6 | 6 | | | | | | | | | | |
| | A Huber | 6 | 6$^4$ | 2 | 6 | J Halard-Decugis | 1 | 2 | | | | | | | | | | |
| 6 | J Halard-Decugis | 4 | 7$^7$ | 6 | | | | | | | | | | 1 | L Davenport | 4 | 6 | 6 |
| | | | | | | | | | | | | | | | R Dragomir | 6 | 2 | 0 |
| | | | | | 4 | J Novotná | 6$^5$ | 0 | | | | | | | | | | |
| | S Farina | 5 | 7$^9$ | 5 | | R Dragomir | 7$^7$ | 6 | | | | | | | | | | |
| | R Dragomir | 7 | 6$^7$ | 7 | | | | | | R Dragomir | 5 | 6 | 7 | | | | | |
| Q | Á Montolio | 6 | 4 | 2 | | | | | 8 | S Testud | 7 | 4 | 5 | | | | | |
| Q | B Schwartz | 4 | 6 | 6 | Q | B Schwartz | 4 | 2 | | | | | | | | | | |
| WC | T Snyder | 6$^4$ | 3 | | 8 | S Testud | 6 | 6 | | | | | | | | | | |
| 8 | S Testud | 7$^7$ | 6 | | | | | | | | | | | | | | | |

### Bottom half

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Quarterfinals | Quarterfinals | Quarterfinals | Quarterfinals | Semifinals | Semifinals | Semifinals | Semifinals |
| 5 | A Coetzer | 6 | 4 | 6 | | | | | | | | | | | | | |
| Q | A Cocheteux | 3 | 6 | 1 | 6 | A Coetzer | 5 | | | | | | | | | | |
| Q | S Appelmans | 3 | 6 | 6 | Q | S Appelmans | 4$^r$ | | | | | | | | | | |
| | S Plischke | 6 | 1 | 4 | | | | | | 6 | A Coetzer | 2 | 1 | | | | |
| | E Likhovtseva | 4 | 7 | 7 | | | | | | 3 | M Seles | 6 | 6 | | | | |
| | L Raymond | 6 | 5 | 5 | | E Likhovtseva | 0 | 6$^6$ | | | | | | | | | |
| | | | | | 3 | M Seles | 6 | 7$^8$ | | | | | | | | | |
| | | | | | | | | | | | | | | 3 | M Seles | 1 | 3 |
| 7 | N Tauziat | 6 | 3 | 3 | | | | | | | | | | 2 | V Williams | 6 | 6 |
| | H Nagyová | 3 | 6 | 6 | | H Nagyová | 6$^5$ | 6 | 3 | | | | | | | | |
| WC | L Osterloh | 3 | 3 | | Q | M Serna | 7$^7$ | 3 | 6 | | | | | | | | |
| Q | M Serna | 6 | 6 | | | | | | | Q | M Serna | 0 | 4 | | | | |
| Q | M Sánchez Lorenzo | 6 | 5 | 6 | | | | | | 2 | V Williams | 6 | 6 | | | | |
| | D Van Roost | 2 | 7 | 2 | Q | M Sánchez Lorenzo | 1 | 1 | | | | | | | | | |
| | | | | | 2 | V Williams | 6 | 6 | | | | | | | | | |

## Qualifying
### Seeds

* Anne Kremer (qualifying competition)
* Sarah Pitkowski (second round)
* María Sánchez Lorenzo (Qualifier)
* Magüi Serna (Qualifier)
* replaced by Melissa Mazzotta (qualifying competition)
* Alexandra Stevenson (second round)
* Anna Smashnova (second round)
* Gala León García (second round)
* Fabiola Zuluaga (second round)
* Cristina Torrens Valero (qualifying competition)
* Barbara Rittner (second round)
* Barbara Schwartz (Qualifier)
* Cara Black (qualifying competition)
* Katarina Srebotnik (second round)
* Inés Gorrochategui (qualifying competition)
* Marlene Weingärtner (second round)

### Qualifiers

* Tatiana Panova
* Amélie Cocheteux
* Magüi Serna
* Sabine Appelmans
* Barbara Schwartz
* María Sánchez Lorenzo
* Květa Hrdličková
* Ángeles Montolio

## Qualifying 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

### First qualifier

| First round | First round | First round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | 1 | Anne Kremer | 6 | 4 | | | | | |
| Larissa Schaerer | 6 | 2 | | Emmanuelle Gagliardi | 0 | 1$^r$ | | | | | |
| Emmanuelle Gagliardi | 7 | 6 | | | | | 1 | Anne Kremer | 3 | 7 | 6 |
| Meghann Shaughnessy | 4 | 3 | | | | | | Tatiana Panova | 6 | 6 | 7 |
| Tatiana Panova | 6 | 6 | | Tatiana Panova | 6 | 7 | | | | | |
| | | | 11 | Barbara Rittner | 4 | 5 | | | | | |

### Second qualifier

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | 16 | Marlene Weingärtner | 2 | 1 | | | | |
| Alexia Dechaume-Balleret | 6 | 3 | 4 | | Janet Lee | 6 | 6 | | | | |
| Janet Lee | 2 | 6 | 6 | | | | | Janet Lee | 6 | 2 | 4 |
| Alicia Molik | 4 | 6 | 4 | | | | | Amélie Cocheteux | 2 | 6 | 6 |
| Amélie Cocheteux | 6 | 4 | 6 | | Amélie Cocheteux | 6 | 6 | | | | |
| | | | | 6 | Alexandra Stevenson | 4 | 4 | | | | |

### Third qualifier

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | 4 | Magüi Serna | 6 | 1 | 6 | | | | |
| Seda Noorlander | | | | | Meilen Tu | 4 | 6 | 0 | | | | |
| Meilen Tu | w/o | | | | | | | | 4 | Magüi Serna | 6 | 6 |
| Lenka Němečková | 3 | 6 | 6 | | | | | | 13 | Cara Black | 4 | 3 |
| Katarína Studeníková | 6 | 2 | 0 | | Lenka Němečková | 6 | 6 | | | | | |
| | | | | 13 | Cara Black | 4 | 4 | | | | | |

### Fourth qualifier

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | | 10 | Cristina Torrens Valero | w/o | | | | | | |
| | Denisa Chládková | 6 | 6 | | | Denisa Chládková | | | | | | | |
| Alt | Tracy Singian | 2 | 4 | | | | | | 10 | Cristina Torrens Valero | 3 | 6 | 6 |
| | Sabine Appelmans | 2 | 6 | 6 | | | | | | Sabine Appelmans | 6 | 1 | 7 |
| | Kristine Kunce | 6 | 1 | 1 | | Sabine Appelmans | 7 | 6 | | | | | |
| | | | | | 8 | Gala León García | 5 | 2 | | | | | |

### Fifth qualifier

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | Alt | Melissa Mazzotta | 6 | 6 | | | | |
| WC | Linda Wild | 6 | 6 | WC | Linda Wild | 4 | 3 | | | | |
| WC | Jolene Watanabe | 2 | 4 | | | | | Alt | Melissa Mazzotta | 0 | 0$^r$ |
| | Émilie Loit | 6 | 6 | | | | | 12 | Barbara Schwartz | 6 | 3 |
| WC | Patty Murren | 2 | 4 | | Émilie Loit | 2 | 3 | | | | |
| | | | | 12 | Barbara Schwartz | 6 | 6 | | | | |

### Sixth qualifier

| First round | First round | First round | First round | First round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | | 9 | Fabiola Zuluaga | 1 | 2 | | | | |
| | Sandra Kleinová | 3 | 7 | 6 | | Sandra Kleinová | 6 | 6 | | | | |
| WC | Jennifer Hopkins | 6 | 6 | 3 | | | | | | Sandra Kleinová | 4 | 4 |
| | Adriana Serra Zanetti | 4 | 0 | | | | | | 3 | María Sánchez Lorenzo | 6 | 6 |
| | Miriam Oremans | 6 | 6 | | | Miriam Oremans | 4 | 4 | | | | |
| | | | | | 3 | María Sánchez Lorenzo | 6 | 6 | | | | |

### Seventh qualifier

| First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | 7 | Anna Smashnova | 1 | 7 | 3 | | | |
| Virginia Ruano Pascual | 4 | 2 | | Květa Hrdličková | 6 | 6 | 6 | | | |
| Květa Hrdličková | 6 | 6 | | | | | | Květa Hrdličková | 6 | 7 |
| Rita Kuti-Kis | 2 | 6 | | | | | | Nicole Pratt | 4 | 5 |
| Nicole Pratt | 6 | 7 | | Nicole Pratt | 6 | 1 | 6 | | | |
| | | | 14 | Katarina Srebotnik | 4 | 6 | 3 | | | |

### Eighth qualifier

| First round | First round | First round | First round | Second round | Second round | Second round | Second round | Second round | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition | Qualifying competition |
| | | | | 15 | Inés Gorrochategui | 6 | 6 | 3 | | | | | |
| WC | Brandis Braverman | 7 | 6 | WC | Brandis Braverman | 2 | 0 | | | | | | |
| | Magdalena Grzybowska | 5 | 2 | | | | | | 15 | Inés Gorrochategui | 3 | 6 | 3 |
| | Ángeles Montolio | 7 | 6 | | | | | | | Ángeles Montolio | 6 | 0 | 6 |
| | Rita Grande | 6 | 2 | | Ángeles Montolio | 7 | 6 | | | | | | |
| | | | | 2 | Sarah Pitkowski | 5 | 1 | | | | | | |