The 1999 US Open – Men's singles qualifying was a series of tennis matches that took place from August 23 to 26, 1999 to determine the sixteen qualifiers into the main draw of the men's singles tournament, and, if necessary, the lucky losers.
This was the last qualifying pre-tournament appearance of future World No. 1 Roger Federer. He lost in the second round to fellow countryman Ivo Heuberger.
Seeds
Ivan Ljubičić (qualifying competition, lucky loser) Max Mirnyi (qualifying competition, lucky loser) Ronald Agénor (second round) Roger Federer (second round) Antony Dupuis (first round) Davide Sanguinetti (first round) Laurence Tieleman (qualifying competition, lucky loser) Oliver Gross (first round) Xavier Malisse (qualified) Peter Wessels (qualified) Michael Kohlmann (qualified) Adrian Voinea (second round) Lorenzo Manta (qualified) Nicolas Escudé (qualified) Axel Pretsch (qualified) Ville Liukko (qualified) Juan Ignacio Chela (first round) Mikael Tillström (qualifying competition, lucky loser) Oleg Ogorodov (first round) Gastón Etlis (qualifying competition) Nicolás Massú (first round) Vladimir Voltchkov (first round) Christophe Rochus (second round) Vincenzo Santopadre (qualifying competition) Lars Burgsmüller (qualified) Julien Boutter (qualified) Alexander Popp (first round) Mosé Navarra (first round) Fredrik Jonsson (qualified) Tuomas Ketola (qualifying competition) Christian Vinck (second round) Stéphane Huet (qualified)
Qualifiers
Cyril Saulnier Stéphane Huet Fredrik Jonsson Ivo Heuberger Takao Suzuki Cristiano Caratti Julien Boutter Lars Burgsmüller Xavier Malisse Peter Wessels Michael Kohlmann George Bastl Lorenzo Manta Nicolas Escudé Axel Pretsch Ville Liukko
Lucky losers
Ivan Ljubičić Max Mirnyi Laurence Tieleman Mikael Tillström
Qualifying draw
First qualifier
Second qualifier
Third qualifier
Fourth qualifier
Fifth qualifier
Sixth qualifier
Seventh qualifier
Eighth qualifier
Ninth qualifier
Tenth qualifier
Eleventh qualifier
Twelfth qualifier
Thirteenth qualifier
Fourteenth qualifier
Fifteenth qualifier
Sixteenth qualifier
References 1999 US Open – Men's draws and results at the International Tennis Federation