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