| 1 | Winter Wonderland | 1934 |  |
| Guy Lombardo And His Royal Canadians |
| 2 | Winter Wonderland | 1934 | |
| Richard Himber And His Orchestra with Joey Nash |
| 3 | Winter Wonderland | 1934 | |
| Marimba Novelty Orchestra |
| 4 | Winter Wonderland | 1934 | |
| Ted Weems And His Orchestra |
| 5 | Winter Wonderland | 1946 | |
| Johnny Mercer And The Pied Pipers |
| 6 | Winter Wonderland | 1946 | |
| Perry Como And The Satisfiers With Russ Case And His Orchestra |
| 7 | Winter Wonderland | 1946 | |
| Andrews Sisters And Guy Lombardo And His Royal Canadians |
| 8 | Winter Wonderland | 1948 | |
| Buddy Clark With The Girl Friends |
| 9 | Winter Wonderland | 1950 | |
| Ames Brothers |
| 10 | Winter Wonderland | 1955 | |
| The Voices Of Walter Schumann |
| 11 | Winter Wonderland | Dec 1958 | |
| Johnny Mathis |
| 12 | Winter Wonderland | Dec 1959 | |
| Lester Lanin And His Orchestra |
| 13 | Winter Wonderland | Dec 1959 | |
| Roger Williams |
| 14 | Winter Wonderland | Dec 1960 | |
| Ramsey Lewis Trio |
| 15 | Winter Wonderland | Dec 1960 | |
| The Blue Notes |
| 16 | Winter Wonderland | Dec 1963 | |
| Darlene Love |
| 17 | Winter Wonderland | Dec 1964 | |
| Aretha Franklin |
| 18 | Winter Wonderland | Dec 1964 | |
| Doris Day |
| 19 | Winter Wonderland | Dec 1965 | |
| Earl Grant |
| 20 | Winter Wonderland | Dec 1971 | |
| Danny Davis And The Nashville Brass |
| 21 | Winter WonderLand/Silver Bells/White Christmas | Dec 1978 | |
| Carpenters |
| 22 | Winter Wonderland | Dec 1987 | |
| Eurythmics |
| 23 | Winter Wonderland | Dec 1992 | |
| Engelbert Humperdinck |
| 24 | Winter Wonderland | Dec 1992 | |
| Travis Tritt |
| 25 | Winter Wonderland | Dec 1993 | |
| Cocteau Twins |
| 26 | Winter Wonderland | Dec 1994 | |
| Elvis Presley |
| 27 | Winter Wonderland | Dec 2002 | |
| Oak Ridge Boys |
| 28 | Winter Wonderland | Dec 2004 | |
| Clay Aiken |
| 29 | Winter Wonderland | Dec 2004 | |
| Dionne Warwick |
| 30 | Winter Wonderland/White Christmas | Dec 2005 | |
| MercyMe |
| 31 | Winter Wonderland | Dec 2006 | |
| Paul Carrack |
| 32 | Winter Wonderland | Dec 2007 | |
| Sugarland |
| 33 | Winter Wonderland | Dec 2007 | |
| The Isley Brothers Featuring Ronald Isley |
| 34 | Winter Wonderland | Dec 2007 | |
| Brad Paisley |
| 35 | Winter Wonderland | Dec 2007 | |
| Toby Keith |
| 36 | Winter Wonderland | Dec 2008 | |
| Jason Mraz |
| 37 | Winter Wonderland | Dec 2008 | |
| Darius Rucker |
| 38 | Winter Wonderland | Dec 2009 | |
| Al Jarreau |
| 39 | Winter Wonderland | Dec 2009 | |
| Trin-i-tee 5:7 |
| 40 | Winter Wonderland | Dec 2010 | |
| Newsboys |
| 41 | Winter Wonderland | Dec 2011 | |
| Scott Weiland |
| 42 | Winter Wonderland | Dec 2011 | |
| Michael Buble |
| 43 | Winter Wonderland | Dec 2012 | |
| Colbie Caillat |
| 44 | Winter Wonderland | Dec 2012 | |
| Rod Stewart |
| 45 | Winter Wonderland | Dec 2012 | |
| Blake Shelton |
| 46 | Winter Wonderland | Dec 2013 | |
| Foghat |
| 47 | Winter Wonderland/Don't Worry Be Happy | Dec 2014 | |
| Pentatonix |