This is a list of the U.S. Billboard magazine Hot 100 Airplay number-ones of 1999.
| Issue date | Song | Artist(s) |
|---|---|---|
| January 2 | "Have You Ever?" | Brandy |
| January 9 | ||
| January 16 | ||
| January 23 | ||
| January 30 | ||
| February 6 | ||
| February 13 | ||
| February 20 | ||
| February 27 | "Slide" | Goo Goo Dolls |
| March 6 | "Angel of Mine" | Monica |
| March 13 | ||
| March 20 | "No Scrubs" | TLC |
| March 27 | ||
| April 3 | ||
| April 10 | ||
| April 17 | ||
| April 24 | ||
| May 1 | ||
| May 8 | ||
| May 15 | ||
| May 22 | ||
| May 29 | ||
| June 5 | ||
| June 12 | ||
| June 19 | "Livin' La Vida Loca" | Ricky Martin |
| June 26 | ||
| July 3 | ||
| July 10 | ||
| July 17 | "I Want It That Way" | Backstreet Boys |
| July 24 | ||
| July 31 | ||
| August 7 | "All Star" | Smash Mouth |
| August 14 | ||
| August 21 | ||
| August 28 | ||
| September 4 | ||
| September 11 | "Genie in a Bottle" | Christina Aguilera |
| September 18 | ||
| September 25 | ||
| October 2 | "Mambo #5" | Lou Bega |
| October 9 | ||
| October 16 | ||
| October 23 | ||
| October 30 | ||
| November 6 | ||
| November 13 | "Smooth" | Santana featuring Rob Thomas |
| November 20 | ||
| November 27 | ||
| December 4 | ||
| December 11 | ||
| December 18 | "Back At One" | Brian McKnight |
| December 25 |
|
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