This is a list of singles that charted in the top ten of the Billboard Hot 100 during 1999.
Whitney Houston and Faith Evans each had three top-ten hits in 1999, tying them for the most top-ten hits during the year.
| Top ten entry date |
Single | Artist(s) | Peak | Peak date | Weeks in top ten |
|---|---|---|---|---|---|
| Singles from 1998 | |||||
| December 12 | "Have You Ever?" | Brandy | 1 | January 16 | 13 |
| "...Baby One More Time" | Britney Spears | 1 | January 30 | 14 | |
| "Lullaby" | Shawn Mullins | 7 | January 16 | 6 | |
| Singles from 1999 | |||||
| January 2 | "Trippin'" | Total featuring Missy Elliott | 7 | January 9 | 3 |
| January 16 | "Save Tonight" | Eagle-Eye Cherry | 5 | January 23 | 4 |
| January 23 | "Hands" | Jewel | 6 | January 23 | 3 |
| "Slide" | Goo Goo Dolls | 8 | February 13 | 8 | |
| January 30 | "Jumper" | Third Eye Blind | 5 | January 30 | 3 |
| "Angel of Mine" | Monica | 1 | February 13 | 15 | |
| February 6 | "All I Have to Give" | Backstreet Boys | 5 | February 6 | 9 |
| "Angel" | Sarah McLachlan | 4 | March 6 | 8 | |
| February 13 | "Believe" | Cher | 1 | March 13 | 16 |
| "Heartbreak Hotel" | Whitney Houston featuring Faith Evans and Kelly Price | 2 | March 20 | 15 | |
| February 20 | "Faded Pictures" | Case featuring Joe | 10 | February 20 | 1 |
| February 27 | "(God Must Have Spent) A Little More Time on You" | 'N Sync | 8 | February 27 | 2 |
| March 6 | "You" | Jesse Powell | 10 | March 6 | 1 |
| March 13 | "I Still Believe" | Mariah Carey | 4 | March 20 | 7 |
| "Every Morning" | Sugar Ray | 3 | April 3 | 13 | |
| "No Scrubs" | TLC | 1 | April 10 | 17 | |
| March 20 | "Kiss Me" | Sixpence None the Richer | 2 | May 1 | 16 |
| March 27 | "What's It Gonna Be?!" | Busta Rhymes featuring Janet Jackson | 3 | April 17 | 9 |
| April 3 | "All Night Long" | Faith Evans featuring Puff Daddy | 9 | April 3 | 2 |
| April 10 | "Stay the Same" | Joey McIntyre | 10 | April 10 | 2 |
| April 17 | "C'est la Vie" | B*Witched | 9 | April 17 | 2 |
| May 1 | "Livin' la Vida Loca" | Ricky Martin | 1 | May 8 | 14 |
| "Please Remember Me" | Tim McGraw | 10 | May 1 | 1 | |
| May 8 | "Who Dat" | JT Money featuring Solé | 5 | May 22 | 6 |
| May 15 | "Fortunate" | Maxwell | 4 | May 29 | 9 |
| "Give It to You" | Jordan Knight | 10 | May 15 | 1 | |
| May 22 | "Where My Girls At?" | 702 | 4 | June 19 | 19 |
| May 29 | "If You Had My Love" | Jennifer Lopez | 1 | June 12 | 15 |
| "808" | Blaque | 8 | June 12 | 4 | |
| June 5 | "That Don't Impress Me Much" | Shania Twain | 7 | June 12 | 4 |
| June 12 | "Chanté's Got a Man" | Chanté Moore | 10 | June 12 | 2 |
| June 19 | "I Want It That Way" | Backstreet Boys | 6 | June 26 | 11 |
| June 26 | "Last Kiss" | Pearl Jam | 2 | June 26 | 10 |
| "The Hardest Thing" | 98 Degrees | 5 | July 3 | 3 | |
| July 3 | "It's Not Right but It's Okay" | Whitney Houston | 4 | July 3 | 5 |
| July 10 | "Bills, Bills, Bills" | Destiny's Child | 1 | July 17 | 10 |
| "Wild Wild West" | Will Smith featuring Dru Hill and Kool Moe Dee | 1 | July 24 | 6 | |
| July 17 | "Genie in a Bottle" | Christina Aguilera | 1 | July 31 | 14 |
| "All Star" | Smash Mouth | 4 | August 14 | 12 | |
| August 7 | "Tell Me It's Real" | K-Ci & JoJo | 2 | August 14 | 4 |
| "Summer Girls" | LFO | 3 | August 28 | 8 | |
| August 21 | "Jamboree" | Naughty by Nature featuring Zhané | 10 | August 21 | 1 |
| August 28 | "Bailamos" | Enrique Iglesias | 1 | September 4 | 6 |
| September 4 | "Unpretty" | TLC | 1 | September 18 | 14 |
| "Smooth" | Santana featuring Rob Thomas | 1 | October 23 | 30 | |
| "Someday" | Sugar Ray | 7 | October 2 | 7 | |
| September 11 | "Lost in You" ↑ | Chris Gaines | 5 | September 11 | 2 |
| September 18 | "She's All I Ever Had" | Ricky Martin | 2 | September 25 | 5 |
| September 25 | "Mambo No. 5" | Lou Bega | 3 | November 13 | 12 |
| October 2 | "Scar Tissue" | Red Hot Chili Peppers | 9 | October 2 | 4 |
| "I Need to Know" | Marc Anthony | 3 | November 27 | 19 | |
| October 9 | "Heartbreaker" | Mariah Carey featuring Jay-Z | 1 | October 9 | 8 |
| October 16 | "Music of My Heart" | Gloria Estefan and 'N Sync | 2 | October 16 | 3 |
| October 23 | "Satisfy You" | Puff Daddy featuring R. Kelly | 2 | October 30 | 6 |
| "We Can't Be Friends" | Deborah Cox featuring R.L. | 8 | October 23 | 3 | |
| November 6 | "Back at One" | Brian McKnight | 2 | November 20 | 15 |
| "Steal My Sunshine" | Len | 9 | November 13 | 3 | |
| November 13 | "(You Drive Me) Crazy" | Britney Spears | 10 | November 13 | 1 |
| November 20 | "I Wanna Love You Forever" | Jessica Simpson | 3 | December 11 | 10 |
| November 27 | "Waiting for Tonight" | Jennifer Lopez | 8 | December 4 | 4 |
| December 4 | "U Know What's Up" | Donell Jones featuring Lisa Lopes | 7 | December 11 | 6 |
| December 11 | "Girl on TV" | LFO | 10 | December 11 | 2 |
| December 18 | "24/7" | Kevon Edmonds | 10 | December 18 | 2 |
|
Main article: List of Billboard Hot 100 top-ten singles in 1998 |
| Top ten entry date |
Single | Artist(s) | Peak | Peak date | Weeks in top ten |
|---|---|---|---|---|---|
| October 17 | "Because of You" | 98 Degrees | 3 | November 21 | 14 |
| October 24 | "Lately" | Divine | 1 | November 28 | 14 |
| November 7 | "Nobody's Supposed to Be Here" | Deborah Cox | 2 | December 5 | 20 |
| November 14 | "Doo Wop (That Thing)" ↑ | Lauryn Hill | 1 | November 14 | 11 |
| December 5 | "From This Moment On" | Shania Twain | 4 | December 19 | 6 |
| "I'm Your Angel" | Céline Dion and R. Kelly | 1 | December 5 | 10 | |
| "Love Like This" | Faith Evans | 7 | December 12 | 6 |
|
Main article: List of Billboard Hot 100 top-ten singles in 2000 |
| Top ten entry date |
Single | Artist(s) | Peak | Peak date | Weeks in top ten |
|---|---|---|---|---|---|
| October 9 | "My Love Is Your Love" | Whitney Houston | 4 | January 1 | 17 |
| December 4 | "I Knew I Loved You" | Savage Garden | 1 | January 29 | 17 |
| December 18 | "Hot Boyz" | Missy Elliott featuring Lil' Mo, Nas, Eve and Q-Tip | 5 | January 8 | 10 |
| December 25 | "Bring It All to Me" | Blaque | 5 | January 22 | 9 |