ATP Cincinnati Masters 1999 Draw, Results & Schedule

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Pete Sampras won the 1999 Cincinnati Masters, defeating Patrick Rafter 7-6(7) 6-3 in the final. The Masters 1000 event was played on hard courts in Cincinnati, United States, from August 9 to August 16, 1999.

Champion
Pete Sampras
def. Patrick Rafter , 7-6(7) 6-3
Dates
Aug 9 — Aug 16
Location
Cincinnati, United States
Category
Masters 1000
Surface
Hard
Prize money
—
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DateRoundWinnerScoreLoserH2HMatch
F (1)
Aug 16, 1999* F Pete Sampras #1 7-6(7) 6-3 Patrick Rafter #4 H2H Match data
SF (2)
Aug 15, 1999* SF Pete Sampras #1 7-6(7) 6-4 Andre Agassi #3 H2H Match data
Aug 15, 1999* SF Patrick Rafter #4 6-4 6-2 Yevgeny Kafelnikov #2 H2H Match data
QF (4)
Aug 15, 1999* QF Patrick Rafter #4 6-2 6-1 Michael Chang #58 H2H Match data
Aug 15, 1999* QF Pete Sampras #1 6-4 6-2 Richard Krajicek #13 H2H Match data
Aug 15, 1999* QF Andre Agassi #3 6-2 7-6(10) Gustavo Kuerten #6 H2H Match data
Aug 15, 1999* QF Yevgeny Kafelnikov #2 7-5 7-5 Tim Henman #5 H2H Match data
R16 (8)
Aug 14, 1999* R16 Yevgeny Kafelnikov #2 6-4 6-4 Chris Woodruff #86 H2H Match data
Aug 14, 1999* R16 Gustavo Kuerten #6 7-5 7-5 Tommy Haas #15 H2H Match data
Aug 14, 1999* R16 Michael Chang #58 6-1 6-4 Cedric Pioline #26 H2H Match data
Aug 14, 1999* R16 Tim Henman #5 6-4 6-1 Nicolas Kiefer #17 H2H Match data
Aug 14, 1999* R16 Patrick Rafter #4 6-2 6-3 Nicolas Lapentti #21 H2H Match data
Aug 14, 1999* R16 Richard Krajicek #13 6-4 6-2 Justin Gimelstob #105 H2H Match data
Aug 14, 1999* R16 Pete Sampras #1 7-5 7-6(2) Rainer Schuettler #49 H2H Match data
Aug 14, 1999* R16 Andre Agassi #3 7-6(3) 7-6(5) Jiri Novak #42 H2H Match data
R32 (16)
Aug 12, 1999* R32 Jiri Novak #42 7-6(3) 7-6(6) Albert Costa #22 H2H Match data
Aug 12, 1999* R32 Tommy Haas #15 6-0 6-7(1) 6-3 Fabrice Santoro #41 H2H Match data
Aug 12, 1999* R32 Chris Woodruff #86 6-1 7-5 Thomas Enqvist #19 H2H Match data
Aug 12, 1999* R32 Pete Sampras #1 7-6(9) 6-4 Jan Siemerink #48 H2H Match data
Aug 12, 1999* R32 Gustavo Kuerten #6 6-2 6-3 Alberto Martin #54 H2H Match data
Aug 12, 1999* R32 Justin Gimelstob #105 6-4 6-4 Todd Martin #7 H2H Match data
Aug 12, 1999* R32 Richard Krajicek #13 6-1 6-3 Ivan Ljubicic #104 H2H Match data
Aug 12, 1999* R32 Nicolas Kiefer #17 2-6 6-4 7-6(10) Paul Goldstein #97 H2H Match data
Aug 12, 1999* R32 Yevgeny Kafelnikov #2 6-1 6-4 Jonas Bjorkman #43 H2H Match data
Aug 12, 1999* R32 Michael Chang #58 6-3 6-7(5) 6-2 Alex Corretja #8 H2H Match data
Aug 12, 1999* R32 Patrick Rafter #4 7-6(3) 6-3 Daniel Vacek #60 H2H Match data
Aug 12, 1999* R32 Andre Agassi #3 6-4 6-1 Arnaud Di Pasquale — Match data
Aug 12, 1999* R32 Tim Henman #5 6-2 6-1 John Van Lottum — Match data
Aug 12, 1999* R32 Cedric Pioline #26 6-7(5) 7-6(4) 2-0 (ret.) Jim Courier #39 H2H Match data
Aug 12, 1999* R32 Rainer Schuettler #49 7-5 7-6(5) Magnus Larsson #62 H2H Match data
Aug 12, 1999* R32 Nicolas Lapentti #21 6-0 7-6(3) Jan-Michael Gambill #50 H2H Match data
R64 (24)
Aug 11, 1999* R64 Fabrice Santoro #41 7-6(5) 6-3 Byron Black #56 H2H Match data
Aug 11, 1999* R64 Ivan Ljubicic #104 7-6(2) 6-4 Richey Reneberg #208 H2H Match data
Aug 11, 1999* R64 Daniel Vacek #60 6-4 6-4 Cecil Mamiit #85 H2H Match data
Aug 11, 1999* R64 Alberto Martin #54 7-6(3) 6-3 David Prinosil #53 H2H Match data
Aug 11, 1999* R64 Nicolas Lapentti #21 6-2 6-2 Vincent Spadea #29 H2H Match data
Aug 11, 1999* R64 Rainer Schuettler #49 6-4 3-4 (ret.) Thomas Johansson #16 H2H Match data
Aug 11, 1999* R64 Jan Siemerink #48 6-1 6-2 Jan Kroslak — Match data
Aug 11, 1999* R64 Jonas Bjorkman #43 6-4 7-5 Andrei Pavel #45 H2H Match data
Aug 11, 1999* R64 Arnaud Di Pasquale 6-4 6-3 MaliVai Washington #349 — Match data
Aug 11, 1999* R64 Tommy Haas #15 7-5 6-2 Xavier Malisse #110 H2H Match data
Aug 11, 1999* R64 Jan-Michael Gambill #50 4-6 6-3 6-4 Sjeng Schalken #47 H2H Match data
Aug 11, 1999* R64 Thomas Enqvist #19 7-5 7-6(1) Wayne Arthurs #94 H2H Match data
Aug 11, 1999* R64 Justin Gimelstob #105 6-2 6-3 Jason Stoltenberg #59 H2H Match data
Aug 11, 1999* R64 Michael Chang #58 6-3 6-4 Marat Safin #34 H2H Match data
Aug 11, 1999* R64 Jiri Novak #42 6-7(3) 7-5 6-3 Axel Pretzsch #124 H2H Match data
Aug 11, 1999* R64 Todd Martin #7 6-4 5-7 6-2 Ramon Delgado #82 H2H Match data
Aug 11, 1999* R64 Chris Woodruff #86 6-3 6-4 Wayne Ferreira #35 H2H Match data
Aug 11, 1999* R64 Nicolas Kiefer #17 7-5 6-3 Sebastien Grosjean #33 H2H Match data
Aug 11, 1999* R64 Magnus Larsson #62 7-6(5) 6-0 Arnaud Clement #69 H2H Match data
Aug 11, 1999* R64 Paul Goldstein #97 6-3 6-2 Mark Woodforde #74 H2H Match data
Aug 11, 1999* R64 Jim Courier #39 7-6(1) 6-2 Goran Ivanisevic #30 H2H Match data
Aug 11, 1999* R64 Albert Costa #22 6-4 3-6 6-2 Andrew Ilie #52 H2H Match data
Aug 11, 1999* R64 Cedric Pioline #26 6-4 6-1 Carlos Moya #10 H2H Match data
Aug 11, 1999* R64 John Van Lottum 6-3 6-2 Wayne Black #113 — Match data

Most Titles

PlayerTitles
Roger Federer 7
Mats Wilander 4
Andre Agassi 3
Novak Djokovic 3
Pete Sampras 3

Recent Finals

SeasonSurfaceWinnerScoreRunner-upH2HMatch
2025 Hard Carlos Alcaraz 5-0 (ret.) Jannik Sinner H2H Match data
2024 Hard Jannik Sinner 7-6(4) 6-2 Frances Tiafoe H2H Match data
2023 Hard Novak Djokovic 5-7 7-6(7) 7-6(4) Carlos Alcaraz H2H Match data
2022 Hard Borna Coric 7-6(0) 6-2 Stefanos Tsitsipas H2H Match data
2021 Hard Alexander Zverev 6-2 6-3 Andrey Rublev H2H Match data

View full tournament history →

Related Tournaments

View all Masters 1000 champions by year →

Other Masters 1000 tournaments in 1999

Previous editions of Cincinnati Masters

Frequently Asked Questions

Where is Cincinnati Masters held?
Cincinnati Masters is held in Cincinnati, United States.
Who won the most recent Cincinnati Masters?
The 2025 Cincinnati Masters was won by Carlos Alcaraz 5-0.
Who has won the most Cincinnati Masters titles?
Roger Federer has won 7 Cincinnati Masters titles, the most by any player in the Open Era (since 1968).
When was the first Cincinnati Masters played?
The first edition of Cincinnati Masters was held in 1899.
What surface is Cincinnati Masters played on?
Cincinnati Masters is played on hard courts.