The ATP Challenger Series is the second tier tour for professional tennis organised by the Association of Tennis Professionals (ATP). The 1999 ATP Challenger Series calendar comprised 115 tournaments, with prize money ranging from $25,000 up to $125,000.^[1][2]

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
25.01.	Germany	Heilbronn Open	$ 100,000	Carpet (i)	Laurence Tieleman	Michael Kohlmann Filippo Veglio

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
01.02.	United States	Amarillo Challenger	$ 050,000	Hard (i)	Gabriel Trifu	Bob Bryan Mike Bryan
	India	Kolkata Challenger	$ 050,000	Grass	Leander Paes	Noam Behr Eyal Ran
	Germany	Warsteiner Challenger	$ 025,000	Carpet (i)	Vladimir Voltchkov	Michael Kohlmann Filippo Veglio
	Uruguay	Punta del Este Challenger	$ 025,000	Clay	Marcelo Charpentier	Lucas Arnold Ker Marcelo Filippini
08.02.	India	Lucknow Challenger I	$ 050,000	Grass	Tuomas Ketola	Nuno Marques Tom Vanhoudt
	Germany	Volkswagen Challenger	$ 025,000	Carpet (i)	Axel Pretzsch	Adriano Ferreira Maurice Ruah
15.02.	Germany	Warsteiner Challenger Lübeck	$ 025,000	Carpet (i)	Axel Pretzsch	Franz Stauder Patrick Sommer
22.02.	Vietnam	Ho Chi Minh Challenger	$ 050,000	Hard	John van Lottum	Juan Ignacio Carrasco Jairo Velasco Jr.
	United States	Laguna Hills Challenger	$ 050,000	Hard	Sébastien Lareau	Paul Goldstein Brian MacPhie
	France	Cherbourg Challenger	$ 037.500	Hard (i)	Sébastien Grosjean	Michael Hill Andrew Painter

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
01.03.	Singapore	Singapore Challenger	$ 050,000	Hard	Mosé Navarra	Jeff Coetzee Damien Roberts
	France	Grenoble Challenger	$ 037.500	Hard (i)	Julien Boutter	Adam Peterson Chris Tontz
	Germany	Residenza Open Magdeburg	$ 025,000	Carpet (i)	Markus Hantschk	Michael Hill Andrew Painter
08.03.	Ecuador	Salinas Challenger	$ 075,000	Hard	Juan Ignacio Chela	Mariano Hood Sebastián Prieto
	France	Besançon Challenger	$ 025,000	Hard (i)	Ivan Ljubičić	Juan Ignacio Carrasco Jairo Velasco Jr.
	Japan	Kyoto Challenger	$ 025,000	Carpet (i)	Julian Knowle	Julian Knowle Lorenzo Manta
29.03.	Italy	Barletta Challenger	$ 025,000	Clay	Jacobo Díaz	Guillermo Cañas Javier Sánchez

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
05.04.	Italy	Napoli Challenger	$ 100,000	Clay	Juan Carlos Ferrero	Marcos Ondruska Jack Waite
12.04.	Bermuda	XL Bermuda Open	$ 100,000	Clay	Hernán Gumy	Doug Flach Richey Reneberg
	France	Nice Challenger	$ 100,000	Clay	Gastón Gaudio	Martín García Sebastián Prieto
	India	New Delhi Challenger	$ 025,000	Hard	Leander Paes	Noam Behr Eyal Ran
26.04.	Portugal	Espinho Challenger	$ 125,000	Clay	Gastón Gaudio	Joan Balcells Gastón Etlis

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
03.05.	Slovenia	Ljubljana Challenger	$ 125,000	Clay	Vladimir Voltchkov	Massimo Valeri Tom Vanhoudt
10.05.	United States	Birmingham Challenger	$ 050,000	Clay	Francisco Costa	Bob Bryan Mike Bryan
	Israel	Jerusalem Challenger	$ 050,000	Hard	Lior Mor	Jeff Coetzee Tuomas Ketola
24.05.	Bulgaria	Sofia Challenger II	$ 025,000	Clay	Marcello Craca	Karsten Braasch Tomas Behrend
31.05.	Czech Republic	Prostějov Challenger	$ 125,000	Clay	Richard Fromberg	Dinu Pescariu Eric Taino
	Germany	Quelle Cup	$ 050,000	Clay	Ronald Agénor	Nebojša Đorđević Marcos Ondruska
	Great Britain	Surbiton Challenger	$ 050,000	Grass	Sargis Sargsian	Scott Draper Todd Woodbridge

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
07.06.	Portugal	Maia Challenger	$ 125,000	Clay	Juan Carlos Ferrero	Mariano Hood Sebastián Prieto
	Germany	ATU Cup	$ 075,000	Clay	Roberto Carretero	Emilio Benfele Álvarez Dušan Vemić
14.06.	Germany	Nord/LB Open	$ 125,000	Clay	Jens Knippschild	Albert Portas Germán Puentes
	Croatia	Zagreb Challenger	$ 050,000	Clay	Andrea Gaudenzi	Ivan Ljubičić Lovro Zovko
21.06.	Italy	Biella Challenger	$ 025,000	Clay	Nicolás Massú	Filippo Messori Massimo Valeri
	Germany	Wartburg Open	$ 025,000	Clay	Juan Albert Viloca	Mitch Sprengelmeyer Jason Weir-Smith
	Czech Republic	Prague Challenger I	$ 025,000	Clay	Michal Tabara	Michal Tabara Radomír Vašek
28.06.	Italy	Venice Challenger	$ 100,000	Clay	Andrei Pavel	Albert Portas Germán Puentes
	Germany	Müller Cup	$ 050,000	Clay	Younes El Aynaoui	Andrew Painter Byron Talbot
	Switzerland	Lugano Challenger	$ 025,000	Clay	Michal Tabara	Michal Tabara Radomír Vašek
	France	Montauban Challenger	$ 025,000	Clay	Álex López Morón	Simon Aspelin Ota Fukárek

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
05.07.	Belgium	Ostend Challenger	$ 125,000	Clay	Olivier Malcor	Marcos Ondruska Steven Randjelovic
	Great Britain	Bristol Challenger	$ 050,000	Grass	Raemon Sluiter	Jan-Ralph Brandt Jeff Coetzee
	Canada	Granby Challenger	$ 050,000	Hard	Petr Kralert	Kevin Kim Jimy Szymanski
	Germany	Oberstaufen Cup	$ 025,000	Clay	Alexander Popp	Edwin Kempes Petr Luxa
12.07.	Austria	Graz Challenger	$ 100,000	Clay	Tomáš Zíb	Nuno Marques Tom Vanhoudt
	United States	Aptos Challenger	$ 050,000	Hard	Michael Hill	Michael Hill Scott Humphries
	France	Contrexéville Challenger	$ 050,000	Clay	Ronald Agénor	Jérôme Hanquez Régis Lavergne
	Great Britain	Manchester Challenger	$ 050,000	Grass	Igor Gaudi	Jeff Coetzee Neville Godwin
19.07.	Great Britain	Newcastle Challenger	$ 050,000	Clay	Jeff Tarango	Marcus Hilpert Vaughan Snyman
	Italy	Olbia Challenger	$ 050,000	Hard	Stefano Pescosolido	Omar Camporese Giorgio Galimberti
	Netherlands	Scheveningen Challenger	$ 050,000	Clay	Emilio Benfele Álvarez	Eyal Ran Tom Vanhoudt
	Finland	Tampere Challenger	$ 050,000	Clay	Radomír Vašek	Petr Dezort Radomír Vašek
	United States	Winnetka Challenger	$ 050,000	Hard	Alex O'Brien	James Blake Thomas Blake
	Spain	Córdoba Challenger	$ 037.500	Hard	Oleg Ogorodov	Satoshi Iwabuchi Oleg Ogorodov
26.07.	Turkey	Istanbul Challenger	$ 100,000	Hard	Vadim Kutsenko	Gouichi Motomura Oleg Ogorodov
	Great Britain	Edinburgh Challenger	$ 025,000	Clay	Héctor Moretti	Marcus Hilpert Vaughan Snyman

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
02.08.	Poland	Poznań Challenger	$ 100,000	Clay	Galo Blanco	Massimo Ardinghi Davide Sanguinetti
	Spain	Open Castilla y León	$ 100,000	Hard	Cyril Saulnier	Roger Federer Sander Groen
	United States	Lexington Challenger	$ 050,000	Hard	Harel Levy	Michael Sell Gabriel Trifu
	Brazil	Gramado Challenger	$ 025,000	Hard	Jamie Delgado	Antonio Prieto Alexandre Simoni
	Austria	Nettingsdorf Challenger	$ 025,000	Clay	Attila Sávolt	Georg Blumauer Alexander Peya
09.08.	United States	Binghamton Challenger	$ 050,000	Hard	Antony Dupuis	Mitch Sprengelmeyer Jason Weir-Smith
	Brazil	Belo Horizonte Challenger	$ 025,000	Hard	Jamie Delgado	Daniel Melo Antonio Prieto
	Spain	Madrid Challenger	$ 025,000	Hard	Ota Fukárek	Thomas Shimada Myles Wakefield
	Poland	Sopot Challenger	$ 025,000	Clay	Roberto Carretero	Bartłomiej Dąbrowski Michał Gawłowski
	Austria	Vienna Challenger	$ 025,000	Clay	Michel Kratochvil	Julian Knowle Thomas Strengberger
16.08.	Czech Republic	Prague Challenger II	$ 100,000	Clay	Davide Sanguinetti	Petr Kovačka Pavel Kudrnáč
	United States	Bronx Challenger	$ 050,000	Hard	Alexander Popp	Jeff Coetzee Alejandro Hernández
	Germany	Volvo Sylt Open	$ 050,000	Clay	Michel Kratochvil	Rene Nicklisch Attila Sávolt
	Italy	Bressanone Challenger	$ 025,000	Clay	Gianluca Luddi	David Miketa Radovan Světlík
23.08.	Switzerland	Geneva Challenger	$ 050,000	Clay	Michel Kratochvil	Emilio Benfele Álvarez Álex López Morón
	Italy	Manerbio Challenger	$ 025,000	Clay	Attila Sávolt	Thomas Strengberger Massimo Valeri
30.08.	Germany	Black Forest Open	$ 037.500	Clay	Michal Tabara	Joan Balcells Thomas Strengberger

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
06.09.	Ukraine	Kyiv Challenger	$ 075,000	Clay	Emilio Benfele Álvarez	Simon Aspelin Johan Landsberg
	Ecuador	Quito Challenger	$ 075,000	Clay	Nicolás Massú	Paulo Taicher Andrés Zingman
	Germany	Rhein-Main Challenger	$ 025,000	Clay	Rene Nicklisch	Francisco Cabello Michael Kohlmann
	Bulgaria	Sofia Challenger I	$ 025,000	Clay	Marcello Craca	Karsten Braasch Tomas Behrend
13.09.	Romania	Brașov Challenger	$ 050,000	Clay	David Sánchez	Andrei Pavel Gabriel Trifu
	Hungary	Budapest Challenger	$ 025,000	Clay	Stéphane Huet	Harel Levy Noam Okun
	North Macedonia	Skopje Challenger	$ 025,000	Clay	Vasilis Mazarakis	Gergely Kisgyörgy Steven Randjelovic
20.09.	Poland	Szczecin Challenger	$ 125,000	Clay	Andreas Vinciguerra	Aleksandar Kitinov Jack Waite
	United States	Austin Challenger	$ 037.500	Hard	André Sá	Marcos Ondruska Wesley Whitehouse
	Spain	Copa Sevilla	$ 025,000	Clay	Sebastián Prieto	Marcelo Charpentier José Frontera
27.09.	United States	San Antonio Challenger	$ 037.500	Hard	Mark Knowles	Mitch Sprengelmeyer Jason Weir-Smith

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
04.10.	Israel	Tel Aviv Challenger	$ 050,000	Hard	Ctislav Doseděl	Noam Behr Eyal Ran
	United States	Tulsa Challenger	$ 050,000	Hard	André Sá	Jeff Coetzee Alejandro Hernández
11.10.	Spain	Barcelona Challenger	$ 100,000	Clay	Fernando Vicente	Eduardo Nicolás Germán Puentes
	Brazil	São Paulo Challenger	$ 100,000	Clay	Hernán Gumy	Jaime Oncins Daniel Orsanic
	United States	Dallas Challenger	$ 037.500	Hard	André Sá	Paul Kilderry Grant Silcock
18.10.	Egypt	Cairo Challenger	$ 125,000	Clay	Karim Alami	Juan Ignacio Carrasco Jairo Velasco Sr.
	Peru	Lima Challenger	$ 100,000	Clay	Juan Ignacio Chela	Pablo Albano Martín García
	Hong Kong	Hongkong Challenger	$ 050,000	Hard	Stéphane Huet	Neville Godwin Michael Hill
	United States	Houston Challenger	$ 037.500	Hard	Marcos Ondruska	David DiLucia Michael Sell
	Germany	Okal Cup	$ 025,000	Carpet (i)	George Bastl	Petr Pála Pavel Vízner
25.10.	France	Brest Challenger	$ 100,000	Hard (i)	Roger Federer	Martin Damm Max Mirnyi
	Uzbekistan	Samarkand Challenger	$ 025,000	Clay	Oleg Ogorodov	Noam Behr Andrei Stoliarov

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
01.11.	Chile	Santiago Challenger	$ 100,000	Clay	Nicolás Massú	Antonio Prieto Cristiano Testa
	Germany	Lambertz Open by STAWAG	$ 050,000	Carpet (i)	Raemon Sluiter	Lars Burgsmüller Takao Suzuki
	Japan	Yokohama Challenger	$ 025,000	Hard (i)	Lee Hyung-taik	Satoshi Iwabuchi Thomas Shimada
08.11.	Uruguay	Montevideo Challenger	$ 100,000	Clay	Karim Alami	Pablo Albano Martín García
	United States	Miami Challenger	$ 050,000	Hard	Marcos Ondruska	Jocelyn Robichaud Myles Wakefield
15.11.	Argentina	Buenos Aires Challenger	$ 100,000	Clay	Franco Squillari	Guillermo Cañas Martín García
	Andorra	Andorra Challenger	$ 075,000	Hard (i)	Justin Gimelstob	Juan Ignacio Carrasco Jairo Velasco Jr.
	Mexico	Puebla Challenger	$ 025,000	Hard	Michael Sell	Óscar Ortiz Marco Osorio
	United States	Rancho Mirage Challenger	$ 025,000	Hard	Bob Bryan	Thomas Shimada Myles Wakefield
22.11.	Mexico	Guadalajara Challenger	$ 100,000	Clay	Francisco Costa	Thomas Shimada Myles Wakefield
29.11.	Venezuela	Caracas Challenger	$ 100,000	Hard	Younes El Aynaoui	Gastón Etlis Martín Rodríguez
	Germany	Nümbrecht Challenger	$ 050,000	Carpet (i)	George Bastl	Dirk Dier Jens Knippschild
	United States	Urbana Challenger	$ 050,000	Hard	Frédéric Niemeyer	Paul Goldstein Jim Thomas
	India	Lucknow Challenger II	$ 025,000	Grass	Leander Paes	Kristian Pless Paradorn Srichaphan

Date	Country	Tournament	Prizemoney	Surface	Singles champion	Doubles champions
06.12.	United States	Burbank Challenger	$ 037.500	Hard	Cecil Mamiit	Bob Bryan Mike Bryan
	India	Jaipur Challenger	$ 025,000	Grass	Leander Paes	Tomáš Anzari Satoshi Iwabuchi
	Mexico	Mexico City Challenger	$ 025,000	Clay	Federico Browne	Gastón Etlis Damián Furmanski
	Australia	Perth Challenger	$ 025,000	Hard	Paul Kilderry	Paul Kilderry Grant Silcock