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The 1999 Davis Cup World Group qualifying round was held from 24 to 26 September. They were the main play-offs of the 1999 Davis Cup. The winners of the playoffs advanced to the 2000 Davis Cup World Group, and the losers were relegated to their respective Zonal Regions I.

Bold indicates team had qualified for the 2000 Davis Cup World Group.

Date: 24–26 September

The eight losing teams in the World Group first round ties and eight winners of the Zonal Group I final round ties competed in the World Group qualifying round for spots in the 2000 World Group.

Home team	Score	Visiting team	Location	Venue	Door	Surface	Ref.
Austria	3-2	Sweden	Pörtschach	Werzer Arena	Outdoor	Clay	[1]
Zimbabwe	4-1	Chile	Harare	Harare Municipal Centre	Indoor	Hard	[2]
Uzbekistan	0-5	Czech Republic	Tashkent	Yunusabad Tennis Centre	Indoor	Hard	[3]
Ecuador	2-3	Netherlands	Guayaquil	Club Nacional de Guayaquil	Outdoor	Clay	[4]
New Zealand	0-5	Spain	Hamilton	Mystery Creek Events Centre	Indoor	Hard	[5]
Italy	3-2	Finland	Sassari	Torres Tennis Sassari	Outdoor	Clay	[6]
Great Britain	4-1	South Africa	Birmingham	National Indoor Arena	Indoor	Hard	[7]
Romania	1-4	Germany	Bucharest	Arena Club	Outdoor	Clay	[8]

•  Czech Republic,  Germany,  Great Britain,  Italy,  Netherlands,  Spain and  Zimbabwe remain in the World Group in 2000.
•  Austria are promoted to the World Group in 2000.
•  Chile,  Ecuador,  Finland,  New Zealand,  Romania,  South Africa and  Uzbekistan remain in Zonal Group I in 2000.
•  Sweden are relegated to Zonal Group I in 2000.

Austria 3	Werzer Arena, Pörtschach, Austria[1] 24–26 September 1999 Clay		Sweden 2
1 2 3 4 5 1 Markus Hipfl Magnus Norman 6 4 6 3 6 4       2 Stefan Koubek Magnus Gustafsson 6 4 4 6 6 4 4 6 10 8   3 Jürgen Melzer / Alexander Peya Nicklas Kulti / Mikael Tillström 3 6 1 6 4 6       4 Stefan Koubek Magnus Norman 77 65 1 6 4 6 2 6     5 Markus Hipfl Magnus Gustafsson 6 1 6 2 7 5

Zimbabwe 4	Harare Municipal Centre, Harare, Zimbabwe[2] 24–26 September 1999 Hard (indoors)		Chile 1
1 2 3 4 5 1 Byron Black Nicolás Massú 4 6 5 7 6 4 6 2 6 3   2 Wayne Black Marcelo Ríos 7 5 5 7 77 63 77 64     3 Byron Black / Wayne Black Fernando González / Nicolás Massú 6 3 2 6 6 4 2 6 4 6   4 Byron Black Marcelo Ríos 77 63 3 6 6 2 78 66     5 Kevin Ullyett Nicolás Massú 77 65 77 64

Uzbekistan 0	Yunusabad Tennis Centre, Tashkent, Uzbekistan[3] 24–26 September 1999 Hard (indoors)		Czech Republic 5
1 2 3 4 5 1 Vadim Kutsenko Jiří Novák 3 6 3 6 2 6       2 Oleg Ogorodov Daniel Vacek 5 7 3 6 4 6       3 Vadim Kutsenko / Oleg Ogorodov Jiří Novák / David Rikl 3 6 2 6 63 77       4 Oleg Ogorodov Petr Kralert 3 6 2 6         5 Vadim Kutsenko David Rikl 6 4 2 6 3 6

Ecuador 2	Club Nacional de Guayaquil, Guayaquil, Ecuador[4] 24–26 September 1999 Clay		Netherlands 3
1 2 3 4 5 1 Nicolás Lapentti Jan Siemerink 6 4 4 6 6 3 6 2     2 Luis Morejón Sjeng Schalken 69 711 2 6 0 6       3 Andrés Gómez / Nicolás Lapentti Paul Haarhuis / Jan Siemerink 5 7 3 6 5 7       4 Nicolás Lapentti Sjeng Schalken 1 6 3 6 6 0 77 65 6 3   5 Luis Morejón Jan Siemerink 4 6 5 7 6 3 3 6

New Zealand 0	Mystery Creek Events Centre, Hamilton, New Zealand[5] 24–26 September 1999 Hard (indoors)		Spain 5
1 2 3 4 5 1 Mark Nielsen Félix Mantilla 2 6 6 3 6 4 62 77 3 6   2 Brett Steven Francisco Clavet 2 6 4 6 4 6       3 James Greenhalgh / Brett Steven Julián Alonso / Joan Balcells 65 77 61 77 4 6       4 James Greenhalgh Julián Alonso 6 3 1 6 3 6       5 Mark Nielsen Francisco Clavet 0 6 4 6

Italy 3	Torres Tennis Sassari, Sassari, Italy[6] 24–26 September 1999 Clay		Finland 2
1 2 3 4 5 1 Andrea Gaudenzi Jarkko Nieminen 6 2 6 3 7 5       2 Davide Sanguinetti Ville Liukko 3 6 6 1 62 77 6 4 3 6   3 Andrea Gaudenzi / Diego Nargiso Tuomas Ketola / Ville Liukko 6 1 4 6 4 6 6 4 2 6   4 Andrea Gaudenzi Ville Liukko 6 3 65 77 2 6 6 1 6 3   5 Davide Sanguinetti Tuomas Ketola 6 2 6 2 1 6 6 1

Great Britain 4	National Indoor Arena, Birmingham, England[7] 24–26 September 1999 Hard (indoors)		South Africa 1
1 2 3 4 5 1 Greg Rusedski Neville Godwin 6 4 4 6 6 4 6 3     2 Tim Henman Grant Stafford 6 3 7 5 78 66       3 Neil Broad / Tim Henman David Adams / John-Laffnie de Jager 3 6 64 77 4 6       4 Tim Henman Neville Godwin 6 2 6 2 6 2       5 Greg Rusedski Grant Stafford 6 4 7 5

Romania 1	Arena Club, Bucharest, Romania[8] 24–26 September 1999 Clay		Germany 4
1 2 3 4 5 1 Adrian Voinea Tommy Haas 5 7 2 6 6 3 1 6     2 Andrei Pavel Rainer Schüttler 77 62 6 2 6 2       3 Andrei Pavel / Gabriel Trifu Marc-Kevin Goellner / David Prinosil 4 6 0 6 3 6       4 Andrei Pavel Tommy Haas 4 6 2 6 64 77       5 Adrian Voinea Marc-Kevin Goellner 4 6 66 78

• Davis Cup official website