| Position | Title | Main Artist | Main Genre | Release Date | Up Vote(s) | Down Vote(s) | |
|---|---|---|---|---|---|---|---|
| 1 | A Winter Romance | Dean Martin | Pop | 1959-01-01 | |||
| 2 | Let It Snow! Let It Snow! Let It Snow! | Dean Martin | Pop | 1959-01-01 | |||
| 3 | The Things We Did Last Summer | Dean Martin | Pop | 1959-01-01 | |||
| 4 | I've Got My Love To Keep Me Warm | Dean Martin | Pop | 1959-01-01 | |||
| 5 | June in January | Dean Martin | Pop | 1959-01-01 | |||
| 6 | Canadian Sunset | Dean Martin | Pop | 1959-01-01 | |||
| 7 | Winter Wonderland | Dean Martin | Pop | 1959-01-01 | |||
| 8 | Out in the Cold Again | Dean Martin | Pop | 1959-01-01 | |||
| 9 | Baby, It's Cold Outside | Dean Martin | Pop | 1959-01-01 | |||
| 10 | Rudolph, the Red-Nosed Reindeer | Dean Martin | Pop | 1959-01-01 | |||
| 11 | White Christmas | Dean Martin | Pop | 1959-01-01 | |||
| 12 | It Won't Cool Off | Dean Martin | Pop | 1959-01-01 |