The 1999 Acura Classic singles was the singles event of the twentieth edition of the third tournament in the US Open Series.

Lindsay Davenport was the defending champion, but she was defeated in the semifinals by Julie Halard-Decugis. Serena Williams then defeated Halard-Decugis in the final to win the title.^[1][2]

	Semifinals							Final
	1	Lindsay Davenport	3	5
		Julie Halard-Decugis	6	7
									Julie Halard-Decugis	1	4
								6	Serena Williams	6	6
	6	Serena Williams	6	7
	2	Martina Hingis	3	5

	First round							Second round							Quarterfinals							Semifinals
								1	L Davenport	6	6
	WC	A Stevenson	4	4					A Huber	2	2
		A Huber	6	6											1	L Davenport	67	6	6
		C Martínez	6	6												C Martínez	79	3	2
		S Plischke	3	3					C Martínez	7	6
	WC	C Morariu	6	6				WC	C Morariu	5	2
	8	S Testud	1	3																		1	L Davenport	3	5
																							J Halard-Decugis	6	7
								3	M Pierce	6	7
		A Sugiyama	6	6					A Sugiyama	2	5
		N Dechy	2	3											3	M Pierce	5	2
	WC	I Majoli	1	4												J Halard-Decugis	7	6
		J Halard-Decugis	6	6					J Halard-Decugis	77	7
		A Frazier	3	7	6				A Frazier	65	5
	5	N Tauziat	6	5	2

	First round							Second round							Quarterfinals							Semifinals
	6	S Williams	4	6	6
		E Likhovtseva	6	3	1			6	S Williams	6	6
		P Schnyder	6	6					P Schnyder	3	1
	Q	M Serna	3	4											6	S Williams	6	6
		R Dragomir	2	710	6										4	A Sánchez Vicario	2	3
	Q	A Kremer	6	68	2				R Dragomir	3	1
								4	A Sánchez Vicario	6	6
																						6	S Williams	6	7
	7	B Schett	6	6																		2	M Hingis	3	5
	Q	I Gorrochategui	3	2				7	B Schett	2	4
		I Spîrlea	4	79	5				N Zvereva	6	2r
		N Zvereva	6	67	7										7	B Schett	79	3	3
		M Lučić	3	1											2	M Hingis	67	6	6
	Q	L Raymond	6	6				Q	L Raymond	1	6	3
								2	M Hingis	6	4	6

	First round							Second round							Qualifying competition
	1	Lisa Raymond	6	6
	WC	Vanessa Webb	0	3
								1	Lisa Raymond	6	77
									Elena Dementieva	1	64
		Elena Dementieva	6	6
		Christína Papadáki	4	3
															1	Lisa Raymond	6	6
															7	Anne-Gaëlle Sidot	2	2
		Pavlina Stoyanova	6	6
		Alicia Molik	4	4
									Pavlina Stoyanova	7	3	4
								7	Anne-Gaëlle Sidot	5	6	6
		Cătălina Cristea	2	1
	7	Anne-Gaëlle Sidot	6	6

	First round							Second round							Qualifying competition
	3	Magüi Serna	6	6
	WC	Meghann Shaughnessy	3	4
								3	Magüi Serna	6	6
									Adriana Serra Zanetti	3	4
		Adriana Serra Zanetti	5	77	7
		Nicole Pratt	7	60	5
															3	Magüi Serna	6	4	6
																Kimberly Po	4	6	4
		Kimberly Po	6	6
		Jane Chi	1	2
									Kimberly Po	7	6
								5	Kristina Brandi	5	2
	WC	Nirupama Vaidyanathan	1	2
	5	Kristina Brandi	6	6

	First round							Second round							Qualifying competition
	6	Fabiola Zuluaga	6	6
		Els Callens	0	0
								6	Fabiola Zuluaga	5	3
									Inés Gorrochategui	7	6
		Inés Gorrochategui	6	6
	WC	Jennifer Hopkins	1	3
																Inés Gorrochategui	5	6	6
																Jana Nejedly	7	2	4
		Janet Lee	2	4
		Elena Tatarkova	6	6
									Elena Tatarkova	2	2
									Jana Nejedly	6	6
		Jana Nejedly	7	6
	4	Cara Black	5	2

	First round							Second round							Qualifying competition
	6	Katarina Srebotnik	4	62
		Meilen Tu	6	77
									Meilen Tu	2	1
									Larisa Neiland	6	6
		Larisa Neiland	4	7	6
	WC	Sarah Taylor	6	5	1
																Larisa Neiland	1	1r
															2	Anne Kremer	6	4
		Tatiana Panova	77	3	6
		Marlene Weingärtner	63	6	0
									Tatiana Panova	4	65
								2	Anne Kremer	6	77
		Jolene Watanabe	4	2
	2	Anne Kremer	6	6

• ITF tournament draws
• Serena Williams v. Martina Hingis - semifinal on YouTube