brown #
= weekly rock chart peak
blue #
= pop chart peak
| 26 | What It's Like | 1 | 5 | Apr 1999 |  |
| Everlast |
| 27 | Bailamos | 1 | Aug 1999 | |
| Enrique Iglesias |
| 28 | Summer Girls | 1 | Jul 1999 | |
| LFO |
| 29 | We Like To Party! | 2 | Feb 1999 | |
| Vengaboys |
| 30 | Mambo No. 5 (A Little Bit Of...) | 2 | Oct 1999 | |
| Lou Bega |
| 31 | Miami | 2 | Jan 1999 | |
| Will Smith |
| 32 | Thinking Of You (I Drive Myself Crazy) | 1 | Apr 1999 | |
| 'NSYNC |
| 33 | Stay The Same | 1 | Mar 1999 | |
| Joey McIntyre |
| 34 | I Do (Cherish You) | 1 | Aug 1999 | |
| 98 Degrees |
| 35 | Last Kiss | 1 | 2 | Jun 1999 | |
| Pearl Jam |
| 36 | That Don't Impress Me Much | 2 | May 1999 | |
| Shania Twain |
| 37 | Wild Wild West | 1 | Jun 1999 | |
| Will Smith Featuring Dru Hill And Kool Moe Dee |
| 38 | Waiting For Tonight | 1 | Nov 1999 | |
| Jennifer Lopez |
| 39 | Where My Girls At? | 2 | Jul 1999 | |
| 702 |
| 40 | Give It To You | 3 | May 1999 | |
| Jordan Knight |
| 41 | Someday | 2 | Aug 1999 | |
| Sugar Ray |
| 42 | My Love Is Your Love | 3 | Oct 1999 | |
| Whitney Houston |
| 43 | (You Drive Me) Crazy | 1 | Oct 1999 | |
| Britney Spears |
| 44 | I Will Remember You LIVE | 2 | Jul 1999 | |
| Sarah McLachlan |
| 45 | Why Don't You Get A Job? | 1 | 3 | May 1999 | |
| The Offspring |
| 46 | Back 2 Good | 5 | Mar 1999 | |
| Matchbox 20 |
| 47 | Bills, Bills, Bills | 2 | Jul 1999 | |
| Destiny's Child |
| 48 | Sometimes | 3 | Jun 1999 | |
| Britney Spears |
| 49 | My Name Is | 2 | 2 | Apr 1999 | |
| Eminem |
| 50 | She's All I Ever Had | 2 | Sep 1999 | |
| Ricky Martin |