Favourite Songs of 1999
| Rank | Song Title | Artist |
| 1 | You Drive Me Crazy | Britney Spears |
| 2 | Waiting For Tonight | Jennifer Lopez |
| 3 | I Believe In You | Amanda Marshall |
| 4 | Pictures | Boomtang Boys |
| 5 | Black Balloon | Goo Goo Dolls |
| 6 | Genie In A Bottle | Christina Aguilera |
| 7 | Sucks To Be You | Prozzak |
| 8 | No Scrubs | TLC |
| 9 | If I Didn't Have You | Amanda Marshall |
| 10 | Feeling Alright | Len |
| 11 | Shave | Sky |
| 12 | Dark Horse | Amanda Marshall |
| 13 | Smooth | Santana |
| 14 | Wild Thing/Poor Boy | Prozzak |
| 15 | Adia | Sarah McLachlan |
| 16 | Where Are My Girls At? | 702 |
| 17 | Iris | Goo Goo Dolls |
| 18 | So Young | The Corrs |
| 19 | My Love Is Your Love | Whitney Housten |
| 20 | Ironic | Alanis Morrisette |
| 21 | Heartbreaker | Mariah Carey |
| 22 | Into You | Three Deep |
| 23 | Hand In My Pocket | Alanis Morrisette |
| 24 | There She Goes | Six Pence None The Richer |
| 25 | Blue | Eiffel 65 |
| 26 | Girlfriend | Billie |
| 27 | Baby One More Time | Britney Spears |
| 28 | Strong Enough | Cher |
| 29 | Building A Mystery | Sarah McLachlan |
| 30 | Unpretty | TLC |
| 31 | Evisa | The Venga Boys |
| 32 | From The Bottom Of My Broken Heart | Britney Spears |
| 33 | Strange Disease | Prozzak |
| 34 | I Need To Know | Anthony |
| 35 | Never Gonna Give Up | 3 Deep |
| 36 | Anywhere But Here | K.D. Lang |
| 37 | Before You | Chantel Kreviazuk |
| 38 | Angels | Robbie Williams |
| 39 | You And Me | Kim Stockwood |
| 40 | Love Wins Everytime | McMaster And James |
| 41 | Some Kinda Wonderful | Sky |
| 42 | Father And Son | Boyzone |
| 43 | Saying I Love You | The Moffats |
| 44 | Born To Make You Happy | Britney Spears |
| 45 | What's My Age Again | Blink 182 |
| 46 | Email My Heart | Britney Spears |
| 47 | Out Of My Head | Fastball |
| 48 | So Pure | Alanis Morrisette |
| 49 | I Love You | Martina McBride |
| 50 | Love Song | Sky |
| 51 | Bailamos | Enrique |
| 52 | Put Your Lights On | Big Suga |
| 53 | You'll Be In My Heart | Phil Collins |
| 54 | Scar Tissue | The Red Hot Chili Peppers |
| 55 | If You Had My Love | Jennifer Lopez |
| 56 | Cup Of Life | Ricky Martin |
| 57 | I Will Be There | Britney Spears |
| 58 | When You're Gone | Bryan Adams |
| 59 | Bills Bills Bills | Destiny's Child |
| 60 | Heaven Coming Down | The Tea Party |
| 61 | Larger Than Life | The Backstreet Boys |
| 62 | Love Lift Me | Amanda Marshall |
| 63 | The Final Countdown | Europe |
| 64 | Beautiful Stranger | Madonna |
| 65 | Ahead By A Century | 20 |
| 66 | Love Fool | The Cardigans |
| 67 | 12 Years Old | Kim Stockwood |
| 68 | Abracadabra | Sugar Ray |
| 69 | I Wanna Love You Forever | Jessica Simpson |
| 70 | One Week | Barenaked Ladies |
| 71 | Reflection | Christina Aguilera |
| 72 | Sometimes | Britney Spears |
| 73 | Candy | Mandy Moore |
| 74 | Sweet Surrender | Sarah McLachlan |
| 75 | Back At One | Brian McNight |
| 76 | I Drive Myself Crazy | Nsync |
| 77 | Get You In The Morning | The Crash Test Dummies |
| 78 | Fall From Grace | Amanda Marshall |
| 79 | Miss You Like Crazy | The Moffats |
| 80 | I Want It That Way | The Backstreet Boys |