| 1999 Pilot Pen Tennis | |
|---|---|
| Date | August 22–28 |
| Edition | 17th |
| Category | Tier II |
| Draw | 28S / 16D |
| Prize money | $520,000 |
| Surface | Hard / outdoor |
| Location | New Haven, CT, United States |
| Champions | |
| Singles | |
 Venus Williams | |
| Doubles | |
Lisa Raymond /  Rennae Stubbs | |
The 1999 Pilot Pen Tennis was a women's tennis tournament played on outdoor hard courts in New Haven in the United States. It was part of Tier II of the 1999 WTA Tour. The tournament was held from August 22 through August 28, 1999. Second-seeded Venus Williams won the singles title, earning US$ 80,000 first prize money.