The 1999 Pilot Pen Tennis was a women's 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 22 through August 28, 1999. Second-seeded Venus Williams won the singles title, earning US$ 80,000 first prize money.
| 1999 Pilot Pen Tennis | |
|---|---|
| Date | August 22–28 |
| Edition | 17th |
| Category | Tier II |
| Draw | 28S / 16D |
| Prize money | $520,000 |
| Surface | Hard / outdoor |
| Location | New Haven, CT, United States |
| Champions | |
| Singles | |
 Venus Williams | |
| Doubles | |
Lisa Raymond /  Rennae Stubbs | |
Entrants
editSeeds
edit- Ranking date 16 August 1999
| Country | Player | Rank | Seed |
|---|---|---|---|
| USA
|
Lindsay Davenport | 2 | 1 |
| USA
|
Venus Williams | 4 | 2 |
| USA
|
Monica Seles | 5 | 3 |
 CZE
|
Jana Novotná | 7 | 4 |
 RSA
|
Amanda Coetzer | 9 | 5 |
 FRA
|
Julie Halard-Decugis | 11 | 6 |
| FRA
|
Nathalie Tauziat | 12 | 7 |
| FRA
|
Sandrine Testud | 14 | 8 |
Other entrants
editThe 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:
Finals
editSingles
edit Venus Williams defeated Lindsay Davenport, 6–2, 7–5
- This was Williams' fifth title of the year.
Doubles
edit Lisa Raymond / Rennae Stubbs defeated 
Elena Likhovtseva / Jana Novotná, 7–6(7–1), 6–2