Top 40 Hits of Late December 1999
 | 1 | Westlife | I Have A Dream / Seasons In The Sun |
 | 2 | Cliff Richard | The Millennium Prayer |
| 3 | John Lennon | Imagine |
| 4 | Cuban Boys | Cognoscenti vs Intelligentsia |
| 5 | S Club 7 | Two In A Million / You're My Number One |
| 6 | Artful Dodger featuring Craig David | Re-Rewind The Crowd Say Bo Selecta |
| 7 | Mr Hankey | Mr Hankey The Christmas Poo |
| 8 | Steps | Say You'll Be Mine / Better The Devil You Know |
 | 9 | The Vengaboys | Kiss (When The Sun Don't Shine) |
| 10 | William Orbit | Barber's Adagio For Strings |
| 11 | Alice Deejay | Back In My Life |
| 12 | R Kelly | If I Could Turn Back The Hands Of Time |
| 13 | Boyzone | Every Day I Love You |
| 14 | Macy Gray | I Try |
| 15 | The Wamdue Project | King Of My Castle |
| 16 | Len | Steal My Sunshine |
| 17 | Progress Presents The Boy Wunda | Everybody |
 | 18 | DJ Luck & MC Neat | A Little Bit Of Luck |
| 19 | Robbie Williams | She's The One / It's Only Us |
| 20 | Various Artists | It's Only Rock 'N' Roll |
| 21 | Five | Keep On Movin' |
| 22 | Melanie C | Northern Star |
| 23 | Will Smith | Will 2K |
| 24 | B*Witched featuring Ladysmith Black Mambazo | I Shall Be There |
| 25 | Mario Piu | Communication (Somebody Answer The Phone) |
| 26 | Perfect Phase | Horny Horns |
| 27 | Lolly | Big Boys Don't Cry / Rockin' Robin |
| 28 | Celine Dion | That's The Way It Is |
| 29 | Martine McCutcheon | Talking In Your Sleep / Love Me |
| 30 | Tom Jones & Cerys Matthews | Baby, It's Cold Outside |
| 31 | Eiffel 65 | Blue (Da Ba Dee) |
| 32 | Charlotte Church | Just Wave Hello |
| 33 | Queen & David Bowie | Under Pressure '99 |
| 34 | Westlife | Flying Without Wings |
| 35 | Daniel O'Donnell | A Christmas Kiss |
| 36 | Atomic Kitten | Right Now |
| 37 | Whitney Houston | I Learned From The Best |
| 38 | Bob Marley featuring Lauryn Hill | Turn Your Lights Down Low |
| 39 | Christina Aguilera | Genie In A Bottle |
| 40 | Europe | The Final Countdown 2000 |
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