1999 Pilot Pen Tennis
The 1999 Pilot Pen Tennis was a tennis tournament played on outdoor hard courts in New Haven in the United States. It was part of Tier II of the 1999 WTA Tour. The tournament was held from August 23 through August 29, 1999.
| 1999 Pilot Pen Tennis | |
|---|---|
| Date | August 23 – August 29 |
| Edition | 17th |
| Category | Tier II |
| Surface | Hard / Outdoor |
| Location | New Haven, CT, United States |
| Champions | |
| Singles | |
 Venus Williams | |
| Doubles | |
Lisa Raymond / .svg.png.webp){kind=small} Rennae Stubbs | |
Entrants
Seeds
| Country | Player | Rank | Seed |
|---|---|---|---|
| USA |
Lindsay Davenport | 2 | 1 |
| USA |
Venus Williams | 4 | 2 |
| USA |
Monica Seles | 5 | 3 |
 CZE |
Jana Novotná | 9 | 4 |
 RSA |
Amanda Coetzer | 7 | 5 |
 FRA |
Julie Halard-Decugis | 10 | 6 |
| FRA |
Nathalie Tauziat | 12 | 7 |
| FRA |
Sandrine Testud | 16 | 8 |
Other entrants
The following players received wildcards into the singles main draw:
The following players received wildcards into the doubles main draw:
The following players received entry from the singles qualifying draw:
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Champions
Singles
Venus Williams defeated Lindsay Davenport, 6–2, 7–5
- This was Williams' fifth title of the year.
Doubles
Lisa Raymond / Rennae Stubbs defeated 
Elena Likhovtseva / Jana Novotná, 7–6(7–1), 6–2
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