1999 Pilot Pen Tennis

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 23 through August 29, 1999. Second-seeded Venus Williams won the singles title.

Other entrants
The following players received wildcards into the singles main draw:
 * 🇺🇸 Tara Snyder
 * 🇺🇸 Lilia Osterloh

The following players received wildcards into the doubles main draw:
 * 🇺🇸 Tara Snyder / 🇺🇸 Alexandra Stevenson

The following players received entry from the singles qualifying draw:


 * 🇷🇺 Tatiana Panova
 * 🇨🇿 Květa Hrdličková
 * 🇪🇸 Ángeles Montolio
 * 🇦🇹 Barbara Schwartz
 * 🇫🇷 Amélie Cocheteux
 * 🇧🇪 Sabine Appelmans
 * 🇪🇸 Magüi Serna
 * 🇪🇸 María Sánchez Lorenzo

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