Hot 100 number-one hits of 1999 (United States)
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This is a list of the U.S. Billboard magazine Hot 100 number-ones of 1999.
| Issue Date | Song | Artist |
| January 2 | "I'm Your Angel" | R. Kelly and Céline Dion |
| January 9 | "I'm Your Angel" | R. Kelly and Céline Dion |
| January 16 | "Have You Ever?" | Brandy |
| January 23 | "Have You Ever?" | Brandy |
| January 30 | "...Baby One More Time" | Britney Spears |
| February 6 | "...Baby One More Time" | Britney Spears |
| February 13 | "Angel of Mine" | Monica |
| February 20 | "Angel of Mine" | Monica |
| February 27 | "Angel of Mine" | Monica |
| March 6 | "Angel of Mine" | Monica |
| March 13 | "Believe" | Cher |
| March 20 | "Believe" | Cher |
| March 27 | "Believe" | Cher |
| April 3 | "Believe" | Cher |
| April 10 | "No Scrubs" | TLC |
| April 17 | "No Scrubs" | TLC |
| April 24 | "No Scrubs" | TLC |
| May 1 | "No Scrubs" | TLC |
| May 8 | "Livin' la Vida Loca" | Ricky Martin |
| May 15 | "Livin' la Vida Loca" | Ricky Martin |
| May 22 | "Livin' la Vida Loca" | Ricky Martin |
| May 29 | "Livin' la Vida Loca" | Ricky Martin |
| June 5 | "Livin' la Vida Loca" | Ricky Martin |
| June 12 | "If You Had My Love" | Jennifer Lopez |
| June 19 | "If You Had My Love" | Jennifer Lopez |
| June 26 | "If You Had My Love" | Jennifer Lopez |
| July 3 | "If You Had My Love" | Jennifer Lopez |
| July 10 | "If You Had My Love" | Jennifer Lopez |
| July 17 | "Bills, Bills, Bills" | Destiny's Child |
| July 24 | "Wild Wild West" | Will Smith featuring Dru Hill and Kool Moe Dee |
| July 31 | "Genie in a Bottle" | Christina Aguilera |
| August 7 | "Genie in a Bottle" | Christina Aguilera |
| August 14 | "Genie in a Bottle" | Christina Aguilera |
| August 21 | "Genie in a Bottle" | Christina Aguilera |
| August 28 | "Genie in a Bottle" | Christina Aguilera |
| September 4 | "Bailamos" | Enrique Iglesias |
| September 11 | "Bailamos" | Enrique Iglesias |
| September 18 | "Unpretty" | TLC |
| September 25 | "Unpretty" | TLC |
| October 2 | "Unpretty" | TLC |
| October 9 | "Heartbreaker" | Mariah Carey featuring Jay-Z |
| October 16 | "Heartbreaker" | Mariah Carey featuring Jay-Z |
| October 23 | "Smooth" | Santana featuring Rob Thomas |
| October 30 | "Smooth" | Santana featuring Rob Thomas |
| November 6 | "Smooth" | Santana featuring Rob Thomas |
| November 13 | "Smooth" | Santana featuring Rob Thomas |
| November 20 | "Smooth" | Santana featuring Rob Thomas |
| November 27 | "Smooth" | Santana featuring Rob Thomas |
| December 4 | "Smooth" | Santana featuring Rob Thomas |
| December 11 | "Smooth" | Santana featuring Rob Thomas |
| December 18 | "Smooth" | Santana featuring Rob Thomas |
| December 25 | "Smooth" | Santana featuring Rob Thomas |
