Andre Agassi defeated Todd Martin in the final, 6–4, 6–7^(5–7), 6–7^(2–7), 6–3, 6–2 to win the men's singles tennis title at the 1999 US Open. It was his second US Open title and fifth major title overall. With the win, Agassi returned to the world No. 1 singles ranking, ultimately ending Pete Sampras' record streak of six year-end No. 1 rankings.

Pat Rafter was the two-time defending champion, but lost to Cédric Pioline in the first round after succumbing to shoulder tendinitis.

Click on the seed number of a player to go to their draw section.

	Quarterfinals									Semifinals									Final
		Slava Doseděl	3	7	4	4
	7	Todd Martin	6	5	6	6
										7	Todd Martin	6	6	6
											Cédric Pioline	4	1	2
		Cédric Pioline	4	78	716	710
	5	Gustavo Kuerten	6	66	614	68
																			7	Todd Martin	4	77	77	3	2
																			2	Andre Agassi	6	65	62	6	6
	12	Richard Krajicek	60	64	6	6	65
	3	Yevgeny Kafelnikov	77	77	3	1	77
										3	Yevgeny Kafelnikov	6	3	3	3
										2	Andre Agassi	1	6	6	6
	Q	Nicolas Escudé	63	3	4
	2	Andre Agassi	77	6	6

	First round									Second round									Third round									Fourth round
	LL	M Tillström	2	7	4	6	4
		M Safin	6	5	6	2	6				M Safin	2	7	4	6	2
		J Novák	3	6	6	6					J Novák	6	5	6	3	6
		R Delgado	6	4	1	0														J Novák	6	6	5
		J-M Gambill	7	6	6															F Santoro	1	0	1r
		S Koubek	5	1	4						J-M Gambill	4	2	6	79	4r
		F Santoro	5	6	6	1	77				F Santoro	6	6	3	67	4
		S Grosjean	7	4	4	6	62																						J Novák	4	5	7	5
		S Doseděl	6	6	77																								S Doseděl	6	7	5	7
		J Courier	4	4	65						S Doseděl	7	6	6
		F Meligeni	6	7	6						F Meligeni	5	1	3
	WC	K Kim	3	5	1															S Doseděl	77	77	6
	Q	F Jonsson	6	3	77	7													Q	F Jonsson	65	65	3
		A Di Pasquale	4	6	62	5				Q	F Jonsson	6	5	6	7
		F Clavet	3	5	6	4				16	N Lapentti	4	7	4	5
	16	N Lapentti	6	7	4	6

	First round									Second round									Third round									Fourth round
	9	G Rusedski	4	6	6	6
		JC Ferrero	6	2	3	4				9	G Rusedski	6	6	6
		D Prinosil	6	6	6						D Prinosil	4	3	1
		JA Marín	3	2	3														9	G Rusedski	7	3	6	6
	WC	J Blake	2	2	1															C Woodruff	5	6	3	4
		C Woodruff	6	6	6						C Woodruff	6	6	6
		R Schüttler	4	3	4						C Ruud	2	3	3
		C Ruud	6	6	6																							9	G Rusedski	7	6	63	4	4
	WC	B Bryan	3	6	3	4																						7	T Martin	5	0	77	6	6
		M Larsson	6	1	6	6					M Larsson	6	6	3	6
		B Black	65	4	2						Y El Aynaoui	3	4	6	3
		Y El Aynaoui	77	6	6															M Larsson	3	0r
		S Sargsian	3	1	3														7	T Martin	6	0
	WC	R Reneberg	6	6	6					WC	R Reneberg	4	3	6	1
	Q	S Huet	4	3	77	77	63			7	T Martin	6	6	3	6
	7	T Martin	6	6	62	65	77

	First round									Second round									Third round									Fourth round
	4	P Rafter	6	6	3	5	0r
		C Pioline	4	4	6	7	1				C Pioline	77	1	6	3	6
		J Siemerink	1	710	6	3	2			Q	L Burgsmüller	65	6	3	6	2
	Q	L Burgsmüller	6	68	3	6	6													C Pioline	77	7	4	77
		A Portas	6	61	4	4													Q	P Wessels	65	5	6	61
		M Woodforde	3	77	6	6					M Woodforde	6	5	68	64
	Q	P Wessels	4	6	3	77	6			Q	P Wessels	3	7	710	77
		M Zabaleta	6	3	6	63	2																						C Pioline	6	7	6
		H Arazi	6	77	1	6																						14	T Haas	4	5	3
		K Alami	2	64	6	4					H Arazi	3	6	6	77
		F Vicente	6	6	4	712					F Vicente	6	3	3	64
		G Puentes	3	2	6	610														H Arazi	79	3	4	63
		B Karbacher	64	4	2														14	T Haas	67	6	6	77
		M Puerta	77	6	6						M Puerta	3	2	6	77	1
		T Enqvist	2	4	66					14	T Haas	6	6	2	63	6
	14	T Haas	6	6	78

	First round									Second round									Third round									Fourth round
	17	F Mantilla	6	1	2	4
		M Norman	1	6	6	6					M Norman	6	6	6
		G Pozzi	5	77	6	6					G Pozzi	4	3	4
		D Nestor	7	64	1	2														M Norman	4	6	6	6
		M Hipfl	6	6	6															R Fromberg	6	3	1	3
		A Ilie	4	1	2						M Hipfl	7	3	4	4
		W Ferreira	64	6	6	3	65				R Fromberg	5	6	6	6
		R Fromberg	77	4	4	6	77																						M Norman	64	0r
	Q	C Caratti	3	6	2	6	6																					5	G Kuerten	77	0
		J Díaz	6	3	6	2	2			Q	C Caratti	1	6	2	6	4
		G Ivanišević	7	77	4	6					G Ivanišević	6	4	6	2	6
	Q	V Liukko	5	65	6	2														G Ivanišević	4	2	4
		H Dreekmann	4	1	4														5	G Kuerten	6	6	6
		P Haarhuis	6	6	6						P Haarhuis	3	64	6	2
		B Ulihrach	4	4	3					5	G Kuerten	6	77	3	6
	5	G Kuerten	6	6	6

	First round									Second round									Third round									Fourth round
	6	T Henman	61	4	3
		G Cañas	77	6	6						G Cañas	5	63	7	6	3
		J Knippschild	3	77	5	3					V Spadea	7	77	5	3	6
		V Spadea	6	63	7	6														V Spadea	6	4	64	6	77
	Q	J Boutter	5	1r															LL	L Tieleman	2	6	77	2	63
		G Blanco	7	5							G Blanco	4	3	3
	LL	L Tieleman	6	7	6					LL	L Tieleman	6	6	6
	WC	T Dent	4	5	2																								V Spadea	2	63	2
		J van Lottum	6	77	4	713																						12	R Krajicek	6	77	6
	Q	T Suzuki	2	64	6	611					J van Lottum	4	78	6	77
	LL	I Ljubičić	6	6	6					LL	I Ljubičić	6	66	3	65
	WC	J Morrison	1	2	4															J van Lottum	4	1	4
	Q	L Manta	6	6	6														12	R Krajicek	6	6	6
		S Schalken	3	4	3					Q	L Manta	2	4	1
	WC	P King	1	4	0					12	R Krajicek	6	6	6
	12	R Krajicek	6	6	6

	First round									Second round									Third round									Fourth round
	13	À Corretja	3	4	6	6	66
		W Arthurs	6	6	1	4	78				W Arthurs	2	4	77	4
		M Rosset	2	2	0						L Hewitt	6	6	65	6
		L Hewitt	6	6	6															L Hewitt	6	3	6	4	3
		M Rodríguez	3	2	3															A Medvedev	3	6	3	6	6
		A Medvedev	6	6	6						A Medvedev	6	6	6
		S Lareau	3	6	4	6	6				S Lareau	4	1	0
		G Gaudio	6	4	6	1	4																						A Medvedev	65	1	0
		J Tarango	4	4	6	2																						3	Y Kafelnikov	77	6	6
		J Björkman	6	6	1	6					J Björkman	5	6	6	6
		K Carlsen	6	77	6						K Carlsen	7	2	3	3
		H Gumy	4	64	4															J Björkman	1	4	4
	LL	M Mirnyi	3	2	78	77	6												3	Y Kafelnikov	6	6	6
		T Zíb	6	6	66	64	3			LL	M Mirnyi	5	1	77	3
		A Martín	1	6	3	4				3	Y Kafelnikov	7	6	65	6
	3	Y Kafelnikov	6	3	6	6

	First round									Second round									Third round									Fourth round
	8	C Moyá	77	6	6
		D Hrbatý	64	3	4					8	C Moyá	1	4	1r
		M Gustafsson	6	6	66	2	4			Q	N Escudé	6	6	0
	Q	N Escudé	4	4	78	6	6												Q	N Escudé	6	6	6
	Q	I Heuberger	4	3	6	6	3												Q	X Malisse	3	2	1
		C Mamiit	6	6	3	3	6				C Mamiit	6	3	77	66	2
		G Raoux	6	63	2	2				Q	X Malisse	3	6	64	78	6
	Q	X Malisse	3	77	6	6																						Q	N Escudé	6	6	7
		P Goldstein	6	6	6																							10	M Ríos	2	3	5
		S Draper	3	1	0						P Goldstein	7	4	4	3
	WC	M Washington	1	6	63	5					J Krošlák	5	6	6	6
		J Krošlák	6	2	77	7														J Krošlák	3	4	4
	Q	G Bastl	77	4	6	6													10	M Ríos	6	6	6
		F Squillari	64	6	4	4				Q	G Bastl	6	3	2	3
		M Damm	4	65	6	7	1			10	M Ríos	4	6	6	6
	10	M Ríos	6	77	3	5	6

	First round									Second round									Third round									Fourth round
	15	N Kiefer	6	6	1	4	6
		J Stoltenberg	4	3	6	6	3			15	N Kiefer	6	6	6
	Q	M Kohlmann	2	6	6	3	6			Q	M Kohlmann	3	2	2
		A Pavel	6	4	3	6	2												15	N Kiefer	6	4	4	2
		M Filippini	6	3	6	3	2													A Clément	4	6	6	6
		M Chang	3	6	2	6	6				M Chang	3	3	4
		A Clément	6	6	6						A Clément	6	6	6
		W Black	2	3	4																								A Clément	4	4	3
		A Costa	5	3	5																							2	A Agassi	6	6	6
		D Vacek	7	6	7						D Vacek	2	6	6	4	3
		J Gimelstob	6	6	6						J Gimelstob	6	3	2	6	6
		A Gaudenzi	1	3	2															J Gimelstob	1	6	3	4
	Q	A Pretzsch	7	6	6														2	A Agassi	6	4	6	6
	Q	C Saulnier	5	2	3					Q	A Pretzsch	3	2	1
		N Kulti	0	1	3					2	A Agassi	6	6	6
	2	A Agassi	6	6	6

• Association of Tennis Professionals (ATP) – 1999 US Open Men's Singles draw
• 1999 US Open – Men's draws and results at the International Tennis Federation