1999 Great American Insurance ATP Championships – Singles

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.

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

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


 * 1) 🇺🇸 Pete Sampras (champion)
 * 2) 🇦🇺 Patrick Rafter (final)
 * 3) 🇺🇸 Andre Agassi (semifinals)
 * 4) 🇷🇺 Yevgeny Kafelnikov (semifinals)
 * 5) 🇬🇧 Tim Henman (quarterfinals)
 * 6) 🇧🇷 Gustavo Kuerten (quarterfinals)
 * 7)  Richard Krajicek (quarterfinals)
 * 8) 🇪🇸 Álex Corretja (second round)
 * 9) 🇺🇸 Todd Martin (second round)
 * 10) 🇪🇸 Carlos Moyà (first round)
 * 11) 🇩🇪 Tommy Haas (third round)
 * 12) 🇩🇪 Nicolas Kiefer (third round)
 * 13) 🇸🇪 Thomas Enqvist (second round)
 * 14) 🇪🇸 Álbert Costa (second round)
 * 15) 🇪🇨 Nicolás Lapentti (third round)
 * 16) 🇸🇪 Thomas Johansson (first round, retired)

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
• # 🇫🇷 Arnaud Clément

• # 🇦🇺 Mark Woodforde

• # Ramón Delgado

• # 🇩🇪 Axel Pretzsch

• # 🇦🇺 Wayne Arthurs

• # Wayne Black

• # Ivan Ljubičić