Singles
1999 U.S. Men's Clay Court Championships
1998 Champion	Jim Courier
Final
Champion	Magnus Norman[1]
Runner-up	Guillermo Cañas
Score	6–0, 6–3
Events
Singles Doubles
← 1998 · U.S. Men's Clay Court Championships · 2000 →

The 1999 U.S. Men's Clay Court Championships was an Association of Tennis Professionals tennis tournament held in Orlando, Florida in the United States. It was the 31st edition of the tournament and was held from April 19 to April 26. Magnus Norman won the singles title.

A champion seed is indicated in bold text while text in italics indicates the round in which that seed was eliminated.

	First round							Second round							Quarterfinals							Semifinals							Final[1]
	1	J Stoltenberg	6	65	6
		J Gimelstob	0	77	4			1	J Stoltenberg	63	64
		H Gumy	6	62	6				H Gumy	77	77
		T Woodbridge	3	77	4											H Gumy	610	4
		O Stanoytchev	7	0	4										7	C Ruud	712	6
		L Arnold Ker	5	6	6				L Arnold Ker	6	63	2
		Á Calatrava	4	2				7	C Ruud	3	77	6
	7	C Ruud	6	6																		7	C Ruud	2r
	4	M Larsson	6	3	4																		G Cañas	5
		G Pozzi	3	6	6				G Pozzi	3	6	2
		A Martín	6	3	7				A Martín	6	3	6
		J Van Herck	3	6	5											A Martín	4	64
		G Cañas	6	77												G Cañas	6	77
		S Koubek	4	63					G Cañas	6	6
		M Rodríguez	3	4				6	L Hewitt	2	2
	6	L Hewitt	6	6																										Guillermo Cañas	0	3
	WC/5	J Courier	6	7																									8	Magnus Norman	6	6
		M Tillström	4	5				WC/5	J Courier	7	6
	WC	A O'Brien	5	3					G Blanco	5	4
		G Blanco	7	6											WC/5	J Courier	3	77	4
	Q	R Cadart	4	77	6										Q	M Mirnyi	6	63	6
		P Korda	6	64	1			Q	R Cadart	2	67
	Q	M Mirnyi	6	3	6			Q	M Mirnyi	6	79
	3	S Draper	4	6	3																	Q	M Mirnyi	2	1
	8	M Norman	6	6																		8	M Norman	6	6
	Q	O Malcor	3	0				8	M Norman	6	6
		L Tieleman	3	0					C Costa	4	4
		C Costa	6	6											8	M Norman	7	6
	WC	C Woodruff	63	0											Q	G Trifu	5	2
	Q	G Trifu	77	6				Q	G Trifu	6	6
		S Sargsian	3	6	77				S Sargsian	4	4
	2	J-M Gambill	6	3	64