See main article: 1999 Davis Cup. 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 | ||
|---|---|---|---|---|---|---|---|---|
| 3-2 | Outdoor | Clay | ||||||
| 4-1 | Harare Municipal Centre | Indoor | Hard | |||||
| 0-5 | Yunusabad Tennis Centre | Indoor | Hard | |||||
| 2-3 | Club Nacional de Guayaquil | Outdoor | Clay | |||||
| 0-5 | Indoor | Hard | ||||||
| 3-2 | Torres Tennis Sassari | Outdoor | Clay | |||||
| 4-1 | Indoor | Hard | ||||||
| 1-4 | Arena Club | Outdoor | Clay |