brown #
= weekly rock chart peak
blue #
= pop chart peak
| 51 | It's Not Right But It's Okay | 3 | Jun 1999 |  |
| Whitney Houston |
| 52 | Then The Morning Comes | 9 | 6 | Dec 1999 | |
| Smash Mouth |
| 53 | Heartbreak Hotel | 4 | Apr 1999 | |
| Whitney Houston Featuring Faith Evans & Kelly Price |
| 54 | She's So High | 4 | Aug 1999 | |
| Tal Bachman |
| 55 | Beautiful Stranger | 5 | Jul 1999 | |
| Madonna |
| 56 | Tell Me It's Real | 4 | Jul 1999 | |
| K-CI & Jojo |
| 57 | Girl On TV | 3 | Nov 1999 | |
| LFO |
| 58 | Take Me There | 5 | Jan 1999 | |
| BLACKstreet & Mya Featuring Mase & Blinky Blink |
| 59 | Will 2K | 2 | Nov 1999 | |
| Will Smith |
| 60 | C'est La Vie | 4 | Apr 1999 | |
| B*witched |
| 61 | Almost Doesn't Count | 6 | Jun 1999 | |
| Brandy |
| 62 | Scar Tissue | 1 | 6 | Sep 1999 | |
| Red Hot Chili Peppers |
| 63 | Strong Enough | 8 | May 1999 | |
| Cher |
| 64 | The Cup Of Life | 3 | May 1999 | |
| Ricky Martin |
| 65 | Black Balloon | 8 | 6 | Sep 1999 | |
| Goo Goo Dolls |
| 66 | Steal My Sunshine | 5 | 5 | Sep 1999 | |
| Len |
| 67 | Shake Your Bon-Bon | 6 | Nov 1999 | |
| Ricky Martin |
| 68 | What's It Gonna Be?! | 7 | Apr 1999 | |
| Busta Rhymes Featuring Janet Jackson |
| 69 | Fortunate | 8 | Jun 1999 | |
| Maxwell |
| 70 | Suavemente | 10 | Jan 1999 | |
| Elvis Crespo |
| 71 | Satisfy You | 5 | Nov 1999 | |
| Puff Daddy Featuring R. Kelly |
| 72 | The Rockafeller Skank | 11 | 6 | Nov 1999 | |
| Fatboy Slim |
| 73 | I Could Not Ask For More | 10 | Aug 1999 | |
| Edwin McCain |
| 74 | Praise You | 3 | 8 | May 1999 | |
| Fatboy Slim |
| 75 | All Night Long | 7 | Mar 1999 | |
| Faith Evans Featuring Puff Daddy |