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Singles
Singles
1999 Great American Insurance ATP Championships
Final
Champion	Pete Sampras
Runner-up	Patrick Rafter
Score	7–6(9–7), 6–3
Details
Draw	56 (5WC/7Q)
Seeds	16
Events
Singles	Doubles

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.^[1]^[2]

With the win, Sampras reached his fourth title in this season, after previously winning at London (Queen's), Wimbledon and Los Angeles.^[3]

Seeds

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

Pete Sampras (champion)
Patrick Rafter (final)
Andre Agassi (semifinals)
Yevgeny Kafelnikov (semifinals)
Tim Henman (quarterfinals)
Gustavo Kuerten (quarterfinals)
Richard Krajicek (quarterfinals)
Álex Corretja (second round)
Todd Martin (second round)
Carlos Moyà (first round)
Tommy Haas (third round)
Nicolas Kiefer (third round)
Thomas Enqvist (second round)
Álbert Costa (second round)
Nicolás Lapentti (third round)
Thomas Johansson (first round, retired)

Draw

Key

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	4^r										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
WC	P Goldstein	6	6						12	N Kiefer	4	1
Q	M Woodforde	3	2	WC	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	0^r
	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

Qualifying

Qualifying seeds

Arnaud Clément (qualified)
Mark Woodforde (qualified)
Ramón Delgado (qualified)
Bernd Karbacher (qualifying competition)
Wayne Arthurs (qualified)
Martin Damm (qualifying competition)
Ivan Ljubičić (qualified)
Wayne Black (qualified)
Sébastien Lareau (qualifying competition)
Max Mirnyi (qualifying competition)
Axel Pretzsch (qualified)
Mosé Navarra (qualifying competition)
Todd Woodbridge (first round)
Alex O'Brien (qualifying competition)

Qualifiers

Qualifying draw

First qualifier

First round				Qualifying competition

1	Arnaud Clément	6	6

WC	Jeff Morrison	1	2
				1	Arnaud Clément	6	2	7

				14	Alex O'Brien	2	6	5
	Cristiano Caratti	0	3

14	Alex O'Brien	6	6

Second qualifier

First round				Qualifying competition

2	Mark Woodforde	6	6

	Bob Bryan	4	2
				2	Mark Woodforde	6	6

				12	Mosé Navarra	0	3
	Michael Tebbutt	3	1

12	Mosé Navarra	6	6

Third qualifier

First round					Qualifying competition

3	Ramón Delgado	6	2	6

	Barry Cowan	2	6	1
					3	Ramón Delgado	6	6

						Michael Joyce	3	2
	Michael Joyce	6	4	7

13	Todd Woodbridge	3	6	6

Fourth qualifier

First round					Qualifying competition

4	Bernd Karbacher	6	6

WC	Mike Bryan	2	2
					4	Bernd Karbacher	4	5

					11	Axel Pretzsch	6	7
WC	Wynn Criswell	6	3	2

11	Axel Pretzsch	3	6	6

Fifth qualifier

First round					Qualifying competition

5	Wayne Arthurs	4	6	7

	Michael Hill	6	3	6
					5	Wayne Arthurs	6	6

					10	Max Mirnyi	3	4
WC	Marq Foster	3	2

10	Max Mirnyi	6	6

Sixth qualifier

First round					Qualifying competition

6	Martin Damm	4	6	6

	Mark Knowles	6	1	4
					6	Martin Damm	3	2

					8	Wayne Black	6	6
	Kevin Ullyett	0	4

8	Wayne Black	6	6

Seventh qualifier

First round				Qualifying competition

7	Ivan Ljubičić	7	6

	Jared Palmer	6	4
				7	Ivan Ljubičić	6	7

				9	Sébastien Lareau	1	6
	Jonathan Stark	3	3

9	Sébastien Lareau	6	6