brown #
= weekly rock chart peak
blue #
= pop chart peak
| 1 | Pretty Fly (For A White Guy) | 1 | 1 | Jan 1999 |  |
| The Offspring |
| 2 | You Get What You Give | 2 | 10 | Jan 1999 | |
| New Radicals |
| 3 | All I Have To Give | 2 | Jan 1999 | |
| Backstreet Boys |
| 4 | Miami | 2 | Jan 1999 | |
| Will Smith |
| 5 | Take Me There | 5 | Jan 1999 | |
| BLACKstreet & Mya Featuring Mase & Blinky Blink |
| 6 | Let Me Let Go | 12 | Jan 1999 | |
| Faith Hill |
| 7 | Changes | 10 | Feb 1999 | |
| 2Pac Featuring Talent |
| 8 | Unsent | 11 | Feb 1999 | |
| Alanis Morissette |
| 9 | When A Woman's Fed Up | 7 | Feb 1999 | |
| R. Kelly |
| 10 | Sweet Lady | 18 | Feb 1999 | |
| Tyrese |
| 11 | Malibu | 2 | 22 | Mar 1999 | |
| Hole |
| 12 | Back 2 Good | 5 | Mar 1999 | |
| Matchbox 20 |
| 13 | Everybody's Free (To Wear Sunscreen) The Speech Song | 7 | Apr 1999 | |
| Baz Luhrmann |
| 14 | What It's Like | 1 | 5 | Apr 1999 | |
| Everlast |
| 15 | Heavy | 1 | 28 | Apr 1999 | |
| Collective Soul |
| 16 | Crush | 12 | 30 | Apr 1999 | |
| Dave Matthews Band |
| 17 | Wish You Were Here | 29 | Apr 1999 | |
| Mark Wills |
| 18 | Thinking Of You (I Drive Myself Crazy) | 1 | Apr 1999 | |
| 'NSYNC |
| 19 | Why Don't You Get A Job? | 1 | 3 | May 1999 | |
| The Offspring |
| 20 | I'll Think Of A Reason Later | 20 | May 1999 | |
| Lee Ann Womack |
| 21 | Freak Of The Week | 3 | 19 | May 1999 | |
| Marvelous 3 |
| 22 | Special | 3 | 29 | May 1999 | |
| Garbage |
| 23 | I Want It That Way | 1 | May 1999 | |
| Backstreet Boys |
| 24 | Almost Doesn't Count | 6 | Jun 1999 | |
| Brandy |
| 25 | Millennium | 14 | Jun 1999 | |
| Robbie Williams |
| 26 | Sometimes | 3 | Jun 1999 | |
| Britney Spears |
| 27 | Anything But Down | 19 | Jun 1999 | |
| Sheryl Crow |
| 28 | All Star | 1 | 1 | Jul 1999 | |
| Smash Mouth |
| 29 | I Will Remember You LIVE | 2 | Jul 1999 | |
| Sarah McLachlan |
| 30 | Beautiful Stranger | 5 | Jul 1999 | |
| Madonna |
| 31 | You'll Be In My Heart | 21 | Jul 1999 | |
| Phil Collins |
| 32 | Graduation (Friends Forever) | 23 | Jul 1999 | |
| Vitamin C |
| 33 | Hey Leonardo (She Likes Me For Me) | 11 | Jul 1999 | |
| Blessid Union Of Souls |
| 34 | I Could Not Ask For More | 10 | Aug 1999 | |
| Edwin McCain |
| 35 | Bailamos | 1 | Aug 1999 | |
| Enrique Iglesias |
| 36 | She's So High | 4 | Aug 1999 | |
| Tal Bachman |
| 37 | No Matter What | 30 | Aug 1999 | |
| Boyzone |
| 38 | I Do (Cherish You) | 1 | Aug 1999 | |
| 98 Degrees |
| 39 | My Own Worst Enemy | 1 | 26 | Aug 1999 | |
| Lit |
| 40 | Out Of My Head | 11 | Sep 1999 | |
| Fastball |
| 41 | She's All I Ever Had | 2 | Sep 1999 | |
| Ricky Martin |
| 42 | Steal My Sunshine | 5 | 5 | Sep 1999 | |
| Len |
| 43 | What's My Age Again | 2 | 16 | Sep 1999 | |
| Blink 182 |
| 44 | So Anxious | 17 | Sep 1999 | |
| Ginuwine |
| 45 | Larger Than Life | 2 | Sep 1999 | |
| Backstreet Boys |
| 46 | Sunshine | 16 | Oct 1999 | |
| Coko |
| 47 | (You Drive Me) Crazy | 1 | Oct 1999 | |
| Britney Spears |
| 48 | There She Goes | 13 | Oct 1999 | |
| Sixpence None The Richer |
| 49 | American Woman | 2 | 30 | Oct 1999 | |
| Lenny Kravitz |
| 50 | Man! I Feel Like A Woman! | 8 | Oct 1999 | |
| Shania Twain |
| 51 | Back At One | 1 | Oct 1999 | |
| Brian McKnight |
| 52 | Waiting For Tonight | 1 | Nov 1999 | |
| Jennifer Lopez |
| 53 | Gotta Man | 27 | Nov 1999 | |
| Eve |
| 54 | Cowboy | 4 | 15 | Nov 1999 | |
| Kid Rock |
| 55 | Will 2K | 2 | Nov 1999 | |
| Will Smith |
| 56 | Angels | 22 | Nov 1999 | |
| Robbie Williams |
| 57 | Blue (Da Ba Dee) | 1 | Dec 1999 | |
| Eiffel 65 |
| 58 | Somewhere Someday | 13 | Dec 1999 | |
| 'NSYNC |
| 59 | You Don't Know Me | 25 | Dec 1999 | |
| Armand Van Helden Featuring Duane Harden |
| 60 | Then The Morning Comes | 9 | 6 | Dec 1999 | |
| Smash Mouth |
| 61 | Learn To Fly | 1 | 10 | Dec 1999 | |
| Foo Fighters |
| 62 | Bring It All To Me | 2 | Dec 1999 | |
| Blaque Featuring JC Chasez |
| 63 | This Gift | 7 | Dec 1999 | |
| 98 Degrees |
| 64 | The Chanukah Song Part II | 22 | Dec 1999 | |
| Adam Sandler |
| 65 | Rhythm Divine | 13 | Dec 1999 | |
| Enrique Iglesias |