1999 Legg Mason Tennis Classic – Singles

Andre Agassi was the defending champion and won for the second straight year in the final 7–6(7–3), 6–1, over Yevgeny Kafelnikov.

Seeds
• # 🇷🇺 Yevgeny Kafelnikov (final)

• # 🇺🇸 Andre Agassi (champion)

• # 🇬🇧 Tim Henman (third round)

• # 🇺🇸 Todd Martin (semifinals)

• # 🇪🇸 Àlex Corretja (third round)

• # 🇩🇪 Nicolas Kiefer (semifinals)

• # Marc Rosset (third round)

• # 🇷🇺 Marat Safin (third round)

• # 🇫🇷 Fabrice Santoro (quarterfinals)

• # 🇩🇪 Rainer Schüttler (second round)

• # 🇺🇸 Jan-Michael Gambill (third round)

• # Byron Black (first round)

• # 🇺🇸 Michael Chang (second round)

• # 🇸🇰 Ján Krošlák (quarterfinals)

• # 🇦🇺 Richard Fromberg (first round)

• # Marcelo Filippini (first round)

Key

 * WC - Wildcard
 * Q - Qualifier
 * SE - Special Exempt
 * r - Retired

Qualifying seeds
• # 🇸🇪 Mikael Tillström (qualified)

• # Kevin Ullyett (qualified)

• # Marcos Ondruska (first round)

• # Neville Godwin (qualifying competition)

• # 🇦🇺 Michael Hill (qualifying competition)

• # Nenad Zimonjić (qualified)

• # Ivo Heuberger (first round)

• # 🇺🇸 David Caldwell (first round)

• # 🇺🇸 Michael Joyce (qualifying competition)

• # 🇺🇸 Brian MacPhie (first round)

• # 🇬🇧 Barry Cowan (first round)

• # 🇺🇸 Michael Russell (first round)

• # 🇦🇺 Mark Draper (qualifying competition)

• # 🇨🇦 Frédéric Niemeyer (qualifying competition)

Qualifiers
• # 🇸🇪 Mikael Tillström

• # Kevin Ullyett

• # Irakli Labadze

• # 🇩🇪 Björn Phau

• # 🇺🇸 Mashiska Washington

• # Nenad Zimonjić

• # 🇦🇺 Ben Ellwood