Top 40 Hits of May 1999
| 1 | Westlife | Swear It Again |
| 2 | TLC | No Scrubs |
| 3 | Backstreet Boys | I Want It That Way |
| 4 | Boyzone | You Needed Me |
| 5 | Fatboy Slim | Right Here Right Now |
| 6 | Shanks & Bigfoot | Sweet Like Chocolate |
| 7 | Phats & Small | Turn Around |
| 8 | Martine McCutcheon | Perfect Moment |
| 9 | Basement Jaxx | Red Alert |
| 10 | Shania Twain | That Don't Impress Me Much |
| 11 | The Offspring | Why Don't You Get A Job? |
| 12 | Geri Halliwell | Look At Me |
| 13 | Texas | In Our Lifetime |
| 14 | The New Radicals | You Get What You Give |
| 15 | Stereophonics | Pick A Part That's New |
| 16 | Busta Rhymes featuring Janet | What's It Gonna Be?! |
| 17 | The Cartoons | Witch Doctor |
| 18 | 911 | Private Number |
| 19 | Steps, Tina Cousins, Cleopatra, B*Witched & Billie | Thank Abba For The Music |
| 20 | Britney Spears | Baby One More Time |
| 21 | Bryan Adams | Cloud Number 9 |
| 22 | TQ | Bye Bye Baby |
| 23 | Eminem | My Name Is |
| 24 | Sixpence None The Richer | Kiss Me |
| 25 | The Wiseguys | Ooh La La |
| 26 | The Honeyz | Love Of A Lifetime |
| 27 | Precious | Say It Again |
| 28 | Mr Oizo | Flat Beat |
| 29 | Pete Heller | Big Love |
| 30 | Glamma Kid featuring Shola Ama | Taboo |
| 31 | Fierce | Dayz Like That |
| 32 | The Vengaboys | We Like To Party! (The Vengabus) |
| 33 | Cast | Beat Mama |
| 34 | Whitney Houston | It's Not Right But It's Okay |
| 35 | Hepburn | I Quit |
| 36 | Faithless | Bring My Family Back |
| 37 | Steps | Better Best Forgotten |
| 38 | Armand Van Helden featuring Roland Clark | Flowers |
| 39 | 1999 Manchester United Squad | Lift It High (All About Belief) |
| 40 | Jamiroquai | Canned Heat |
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