Top 40 Hits of Late May 1999
 | 1 | Boyzone | You Needed Me |
 | 2 | Shanks & Bigfoot | Sweet Like Chocolate |
 | 3 | Shania Twain | That Don't Impress Me Much |
 | 4 | Geri Halliwell | Look At Me |
 | 5 | Backstreet Boys | I Want It That Way |
 | 6 | TLC | No Scrubs |
 | 7 | Sixpence None The Richer | Kiss Me |
 | 8 | Phats & Small | Turn Around |
 | 9 | Westlife | Swear It Again |
 | 10 | The Wiseguys | Ooh La La |
 | 11 | Precious | Say It Again |
 | 12 | Stereophonics | Pick A Part That's New |
 | 13 | Bryan Adams | Cloud Number 9 |
 | 14 | Basement Jaxx | Red Alert |
 | 15 | The New Radicals | You Get What You Give |
 | 16 | 911 | Private Number |
 | 17 | Hepburn | I Quit |
 | 18 | Martine McCutcheon | Perfect Moment |
 | 19 | 1999 Manchester United Squad | Lift It High (All About Belief) |
 | 20 | The Offspring | Why Don't You Get A Job? |
 | 21 | Jamiroquai | Canned Heat |
 | 22 | Sugar Ray | Every Morning |
 | 23 | Powerhouse featuring Duane Harden | What You Need |
 | 24 | Britney Spears | Baby One More Time |
 | 25 | Super Furry Animals | Northern Lites |
 | 26 | Skunk Anansie | Secretly |
 | 27 | The Cartoons | Witch Doctor |
 | 28 | Fatboy Slim | Right Here Right Now |
 | 29 | Chicane featuring Maire Brennan | Saltwater |
 | 30 | Pete Heller | Big Love |
 | 31 | Steps, Tina Cousins, Cleopatra, B*Witched & Billie | Thank Abba For The Music |
 | 32 | NAS featuring Puff Daddy | Hate Me Now |
 | 33 | Fierce | Dayz Like That |
 | 34 | Travis | Driftwood |
 | 35 | 1000 Clowns | (Not The) Greatest Rapper |
 | 36 | Texas | In Our Lifetime |
 | 37 | Lost Witness | Happiness Happening |
 | 38 | Busta Rhymes featuring Janet | What's It Gonna Be?! |
 | 39 | Eminem | My Name Is |
 | 40 | Supergrass | Pumping On Your Stereo |