The 1999 Pilot Pen Tennis singles was the singles event of the seventeenth edition of the final tournament in the US Open Series. Steffi Graf was the reigning champion, but had retired after the TIG Classic.

Venus Williams defeated Lindsay Davenport in the final to win her first New Haven title.

	Semifinals							Final
	1	Lindsay Davenport	4	6	6
		Ruxandra Dragomir	6	2	0
								1	Lindsay Davenport	2	5
								2	Venus Williams	6	7
	3	Monica Seles	1	3
	2	Venus Williams	6	6

	First round							Second round							Quarterfinals							Semifinals
								1	L Davenport	6	6
		N Dechy	6	6					N Dechy	4	2
	Q	T Panova	1	3											1	L Davenport	6	6
	Q	K Hrdličková	4	6	5											A Mauresmo	1	2
		A Mauresmo	6	3	7				A Mauresmo	6	6
		A Huber	6	64	2			6	J Halard-Decugis	1	2
	6	J Halard-Decugis	4	77	6																	1	L Davenport	4	6	6
																							R Dragomir	6	2	0
								4	J Novotná	65	0
		S Farina	5	79	5				R Dragomir	77	6
		R Dragomir	7	67	7											R Dragomir	5	6	7
	Q	Á Montolio	6	4	2										8	S Testud	7	4	5
	Q	B Schwartz	4	6	6			Q	B Schwartz	4	2
	WC	T Snyder	64	3				8	S Testud	6	6
	8	S Testud	77	6

	First round							Second round							Quarterfinals							Semifinals
	5	A Coetzer	6	4	6
	Q	A Cocheteux	3	6	1			6	A Coetzer	5
	Q	S Appelmans	3	6	6			Q	S Appelmans	4r
		S Plischke	6	1	4										6	A Coetzer	2	1
		E Likhovtseva	4	7	7										3	M Seles	6	6
		L Raymond	6	5	5				E Likhovtseva	0	66
								3	M Seles	6	78
																						3	M Seles	1	3
	7	N Tauziat	6	3	3																	2	V Williams	6	6
		H Nagyová	3	6	6				H Nagyová	65	6	3
	WC	L Osterloh	3	3				Q	M Serna	77	3	6
	Q	M Serna	6	6											Q	M Serna	0	4
	Q	M Sánchez Lorenzo	6	5	6										2	V Williams	6	6
		D Van Roost	2	7	2			Q	M Sánchez Lorenzo	1	1
								2	V Williams	6	6

	First round							Second round							Qualifying competition
								1	Anne Kremer	6	4
		Larissa Schaerer	6	2					Emmanuelle Gagliardi	0	1r
		Emmanuelle Gagliardi	7	6											1	Anne Kremer	3	7	6
		Meghann Shaughnessy	4	3												Tatiana Panova	6	6	7
		Tatiana Panova	6	6					Tatiana Panova	6	7
								11	Barbara Rittner	4	5

	First round							Second round							Qualifying competition
								16	Marlene Weingärtner	2	1
		Alexia Dechaume-Balleret	6	3	4				Janet Lee	6	6
		Janet Lee	2	6	6											Janet Lee	6	2	4
		Alicia Molik	4	6	4											Amélie Cocheteux	2	6	6
		Amélie Cocheteux	6	4	6				Amélie Cocheteux	6	6
								6	Alexandra Stevenson	4	4

	First round							Second round							Qualifying competition
								4	Magüi Serna	6	1	6
		Seda Noorlander							Meilen Tu	4	6	0
		Meilen Tu	w/o												4	Magüi Serna	6	6
		Lenka Němečková	3	6	6										13	Cara Black	4	3
		Katarína Studeníková	6	2	0				Lenka Němečková	6	6
								13	Cara Black	4	4

	First round							Second round							Qualifying competition
								10	Cristina Torrens Valero	w/o
		Denisa Chládková	6	6					Denisa Chládková
	Alt	Tracy Singian	2	4											10	Cristina Torrens Valero	3	6	6
		Sabine Appelmans	2	6	6											Sabine Appelmans	6	1	7
		Kristine Kunce	6	1	1				Sabine Appelmans	7	6
								8	Gala León García	5	2

	First round							Second round							Qualifying competition
								Alt	Melissa Mazzotta	6	6
	WC	Linda Wild	6	6				WC	Linda Wild	4	3
	WC	Jolene Watanabe	2	4											Alt	Melissa Mazzotta	0	0r
		Émilie Loit	6	6											12	Barbara Schwartz	6	3
	WC	Patty Murren	2	4					Émilie Loit	2	3
								12	Barbara Schwartz	6	6

	First round							Second round							Qualifying competition
								9	Fabiola Zuluaga	1	2
		Sandra Kleinová	3	7	6				Sandra Kleinová	6	6
	WC	Jennifer Hopkins	6	6	3											Sandra Kleinová	4	4
		Adriana Serra Zanetti	4	0											3	María Sánchez Lorenzo	6	6
		Miriam Oremans	6	6					Miriam Oremans	4	4
								3	María Sánchez Lorenzo	6	6

	First round							Second round							Qualifying competition
								7	Anna Smashnova	1	7	3
		Virginia Ruano Pascual	4	2					Květa Hrdličková	6	6	6
		Květa Hrdličková	6	6												Květa Hrdličková	6	7
		Rita Kuti-Kis	2	6												Nicole Pratt	4	5
		Nicole Pratt	6	7					Nicole Pratt	6	1	6
								14	Katarina Srebotnik	4	6	3

	First round							Second round							Qualifying competition
								15	Inés Gorrochategui	6	6	3
	WC	Brandis Braverman	7	6				WC	Brandis Braverman	2	0
		Magdalena Grzybowska	5	2											15	Inés Gorrochategui	3	6	3
		Ángeles Montolio	7	6												Ángeles Montolio	6	0	6
		Rita Grande	6	2					Ángeles Montolio	7	6
								2	Sarah Pitkowski	5	1

• ITF results page
• WTA draw archive