Singles
1999 Great American Insurance ATP Championships
Champion	Pete Sampras
Runner-up	Patrick Rafter
Score	7–6(9–7), 6–3
Draw	56
Seeds	16

Pete Sampras defeated the defending champion Patrick Rafter in a rematch of the previous year's final, 7–6^(9–7), 6–3 to win the singles tennis title at the 1999 Cincinnati Masters.

Seeds

The top eight seeds received a bye to the second round.

Draw

Finals

	Semifinals							Final
	1	Pete Sampras	79	6
	3	Andre Agassi	67	4
								1	Pete Sampras	79	6
								2	Patrick Rafter	67	3
	4	Yevgeny Kafelnikov	4	2
	2	Patrick Rafter	6	6

Top half

Section 1

	First round							Second round							Third round							Quarterfinals
								1	P Sampras	711	6
		J Siemerink	6	6					J Siemerink	69	4
		J Krošlák	1	2											1	P Sampras	7	77
		M Larsson	77	6												R Schüttler	5	62
	Q	A Clément	65	0					M Larsson	5	65
		R Schüttler	6	3					R Schüttler	7	77
	16	T Johansson	4	4r																		1	P Sampras	6	6
	9	T Martin	6	5	6																	7	R Krajicek	4	2
	Q	R Delgado	4	7	2			9	T Martin	4	4
		J Gimelstob	6	6					J Gimelstob	6	6
		J Stoltenberg	2	3												J Gimelstob	4	2
	WC	R Reneberg	62	4											7	R Krajicek	6	6
	Q	I Ljubičić	77	6				Q	I Ljubičić	1	3
								7	R Krajicek	6	6

Section 2

	First round							Second round							Third round							Quarterfinals
								3	A Agassi	6	6
		A Di Pasquale	6	6					A Di Pasquale	4	1
	WC	M Washington	4	3											3	A Agassi	77	77
	Q	A Pretzsch	77	5	3											J Novák	63	65
		J Novák	63	7	6				J Novák	77	78
		A Ilie	4	6	2			14	Á Costa	63	66
	14	Á Costa	6	3	6																	3	A Agassi	6	712
	11	T Haas	7	6																		6	G Kuerten	2	610
	WC	X Malisse	5	2				11	T Haas	6	61	6
		B Black	65	3					F Santoro	0	77	3
		F Santoro	77	6											11	T Haas	5	5
		A Martín	77	6											6	G Kuerten	7	7
		D Prinosil	63	3					A Martín	2	3
								6	G Kuerten	6	6

Bottom half

Section 3

	First round							Second round							Third round							Quarterfinals
								5	T Henman	6	6
		J van Lottum	6	6					J van Lottum	2	1
	Q	W Black	3	2											5	T Henman	6	6
		P Goldstein	6	6											12	N Kiefer	4	1
	Q	M Woodforde	3	2					P Goldstein	6	4	610
		S Grosjean	5	3				12	N Kiefer	2	6	712
	12	N Kiefer	7	6																		5	T Henman	5	5
	13	T Enqvist	7	77																		4	Y Kafelnikov	7	7
	Q	W Arthurs	5	61				13	T Enqvist	1	5
		W Ferreira	3	4					C Woodruff	6	7
		C Woodruff	6	6												C Woodruff	4	4
		A Pavel	4	5											4	Y Kafelnikov	6	6
		J Björkman	6	7					J Björkman	1	4
								4	Y Kafelnikov	6	6

Section 4

	First round							Second round							Third round							Quarterfinals
								8	Á Corretja	3	77	2
		M Chang	6	6					M Chang	6	65	6
		M Safin	3	4												M Chang	6	6
		G Ivanišević	61	2												C Pioline	1	4
		J Courier	77	6					J Courier	77	64	0r
		C Pioline	6	6					C Pioline	65	77	2
	10	C Moyà	4	1																			M Chang	2	1
	15	N Lapentti	6	6																		2	P Rafter	6	6
		V Spadea	2	2				15	N Lapentti	6	77
		S Schalken	6	3	4				J-M Gambill	0	63
		J-M Gambill	4	6	6										15	N Lapentti	2	3
	WC	C Mamiit	4	4											2	P Rafter	6	6
		D Vacek	6	6					D Vacek	63	3
								2	P Rafter	77	6

External links

• Main draw