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| Date | Title | Country | Details |
|---|---|---|---|
| 1/2 | I'm Your AngelDetailsArtist: R. Kelly and Céline Dion · Weeks at No. 1 that month: 2 | United States | Artist: R. Kelly and Céline Dion · Weeks at No. 1 that month: 2 |
| 1/16 | Have You Ever?DetailsArtist: Brandy · Weeks at No. 1 that month: 2 | United States | Artist: Brandy · Weeks at No. 1 that month: 2 |
| 1/30 | ...Baby One More TimeDetailsArtist: Britney Spears · Weeks at No. 1 that month: 1 | United States | Artist: Britney Spears · Weeks at No. 1 that month: 1 |
| 2/6 | ...Baby One More TimeDetailsArtist: Britney Spears · Weeks at No. 1 that month: 1 | United States | Artist: Britney Spears · Weeks at No. 1 that month: 1 |
| 2/13 | Angel of MineDetailsArtist: Monica · Weeks at No. 1 that month: 3 | United States | Artist: Monica · Weeks at No. 1 that month: 3 |
| 3/6 | Angel of MineDetailsArtist: Monica · Weeks at No. 1 that month: 1 | United States | Artist: Monica · Weeks at No. 1 that month: 1 |
| 3/13 | BelieveDetailsArtist: Cher · Weeks at No. 1 that month: 3 | United States | Artist: Cher · Weeks at No. 1 that month: 3 |
| 4/3 | BelieveDetailsArtist: Cher · Weeks at No. 1 that month: 1 | United States | Artist: Cher · Weeks at No. 1 that month: 1 |
| 4/10 | No ScrubsDetailsArtist: TLC · Weeks at No. 1 that month: 3 | United States | Artist: TLC · Weeks at No. 1 that month: 3 |
| 5/1 | No ScrubsDetailsArtist: TLC · Weeks at No. 1 that month: 1 | United States | Artist: TLC · Weeks at No. 1 that month: 1 |
| 5/8 | Livin' la Vida LocaDetailsArtist: Ricky Martin · Weeks at No. 1 that month: 4 | United States | Artist: Ricky Martin · Weeks at No. 1 that month: 4 |
| 6/5 | Livin' la Vida LocaDetailsArtist: Ricky Martin · Weeks at No. 1 that month: 1 | United States | Artist: Ricky Martin · Weeks at No. 1 that month: 1 |
| 6/12 | If You Had My LoveDetailsArtist: Jennifer Lopez · Weeks at No. 1 that month: 3 | United States | Artist: Jennifer Lopez · Weeks at No. 1 that month: 3 |
| 7/3 | If You Had My LoveDetailsArtist: Jennifer Lopez · Weeks at No. 1 that month: 2 | United States | Artist: Jennifer Lopez · Weeks at No. 1 that month: 2 |
| 7/17 | Bills, Bills, BillsDetailsArtist: Destiny's Child · Weeks at No. 1 that month: 1 | United States | Artist: Destiny's Child · Weeks at No. 1 that month: 1 |
| 7/24 | Wild Wild WestDetailsArtist: Will Smith featuring Dru Hill and Kool Moe Dee · Weeks at No. 1 that month: 1 | United States | Artist: Will Smith featuring Dru Hill and Kool Moe Dee · Weeks at No. 1 that month: 1 |
| 7/31 | Genie in a BottleDetailsArtist: Christina Aguilera · Weeks at No. 1 that month: 1 | United States | Artist: Christina Aguilera · Weeks at No. 1 that month: 1 |
| 8/7 | Genie in a BottleDetailsArtist: Christina Aguilera · Weeks at No. 1 that month: 4 | United States | Artist: Christina Aguilera · Weeks at No. 1 that month: 4 |
| 9/4 | BailamosDetailsArtist: Enrique Iglesias · Weeks at No. 1 that month: 2 | United States | Artist: Enrique Iglesias · Weeks at No. 1 that month: 2 |
| 9/18 | UnprettyDetailsArtist: TLC · Weeks at No. 1 that month: 2 | United States | Artist: TLC · Weeks at No. 1 that month: 2 |
| 10/2 | UnprettyDetailsArtist: TLC · Weeks at No. 1 that month: 1 | United States | Artist: TLC · Weeks at No. 1 that month: 1 |
| 10/9 | HeartbreakerDetailsArtist: Mariah Carey featuring Jay-Z · Weeks at No. 1 that month: 2 | United States | Artist: Mariah Carey featuring Jay-Z · Weeks at No. 1 that month: 2 |
| 10/23 | SmoothDetailsArtist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 2 | United States | Artist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 2 |
| 11/6 | SmoothDetailsArtist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 4 | United States | Artist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 4 |
| 12/4 | SmoothDetailsArtist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 4 | United States | Artist: Santana featuring Rob Thomas · Weeks at No. 1 that month: 4 |