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.
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:
Tatiana Panova
Květa Hrdličková
Ángeles Montolio
Barbara Schwartz
Amélie Cocheteux
Sabine Appelmans Magüi Serna María Sánchez LorenzoSee main article: article and 1999 Pilot Pen Tennis – Singles. 
Venus Williams defeated Lindsay Davenport, 6–2, 7–5
See main article: article and 1999 Pilot Pen Tennis – Doubles. Lisa Raymond / 
Rennae Stubbs defeated Elena Likhovtseva / Jana Novotná, 7–6(7–1), 6–2