| Top 40 Hits of December 1999 |
| 1 |
Cliff Richard | The Millennium Prayer |
| 2 |
Westlife | I Have A Dream / Seasons In The Sun |
| 3 |
Artful Dodger featuring Craig David | Re-Rewind The Crowd Say Bo Selecta |
| 4 |
Alice Deejay | Back In My Life |
| 5 |
Wamdue Project | King Of My Castle |
| 6 |
John Lennon | Imagine |
| 7 |
Vengaboys | Kiss (When The Sun Don't Shine) |
| 8 |
Boyzone | Every Day I Love You |
| 9 |
R Kelly | If I Could Turn Back The Hands Of Time |
| 10 |
William Orbit | Barber's Adagio For Strings |
| 11 |
Macy Gray | I Try |
| 12 |
Mario Piu | Communication (Somebody Answer The Phone) |
| 13 |
Cuban Boys | Cognoscenti vs Intelligentsia |
| 14 |
S Club 7 | Two In A Million / You're My Number One |
| 15 |
Mr Hankey | Mr Hankey The Christmas Poo |
| 16 |
Melanie C | Northern Star |
| 17 |
Len | Steal My Sunshine |
| 18 |
Steps | Say You'll Be Mine / Better The Devil You Know |
| 19 |
Progress presents The Boy Wunda | Everybody |
| 20 |
Robbie Williams | She's The One / It's Only Us |
| 21 |
Martine McCutcheon | Talking In Your Sleep / Love Me |
| 22 |
Lolly | Big Boys Don't Cry / Rockin' Robin |
| 23 |
Five | Keep On Movin' |
| 24 |
Celine Dion | That's The Way It Is |
| 25 |
Atomic Kitten | Right Now |
| 26 |
Will Smith | Will 2K |
| 27 |
B*Witched featuring Ladysmith Black Mambazo | I Shall Be There |
| 28 |
Bob Marley featuring Lauryn Hill | Turn Your Lights Down Low |
| 29 |
Whitney Houston | I Learned From The Best |
| 30 |
Queen & David Bowie | Under Pressure '99 |
| 31 |
DJ Luck & MC Neat | A Little Bit Of Luck |
| 32 |
Tom Jones & Cerys Matthews | Baby, It's Cold Outside |
| 33 |
Eiffel 65 | Blue (Da Ba Dee) |
| 34 |
Various Artists | It's Only Rock 'N' Roll |
| 35 |
Daniel O'Donnell | A Christmas Kiss |
| 36 |
Christina Aguilera | Genie In A Bottle |
| 37 |
Westlife | Flying Without Wings |
| 38 |
Geri Halliwell | Lift Me Up |
| 39 |
Corrs | Radio |
| 40 |
Perfect Phase | Horny Horns |
