| 1 | It's The Most Wonderful Time Of The Year | Dec 1963 |  |
| Andy Williams with Robert Mersey Orchestra |
| 2 | It's The Most Wonderful Time Of The Year | Dec 1986 | |
| Johnny Mathis |
| 3 | It's The Most Wonderful Time Of The Year | Dec 1992 | |
| Amy Grant |
| 4 | It's The Most Wonderful Time Of The Year | Dec 1993 | |
| David Foster With Johnny Mathis |
| 5 | It's The Most Wonderful Time Of The Year | Dec 2004 | |
| Dionne Warwick |
| 6 | It's The Most Wonderful Time Of The Year | Dec 2007 | |
| Captain & Tennille |
| 7 | It's The Most Wonderful Time Of The Year | Dec 2008 | |
| BarlowGirl |
| 8 | The Most Wonderful Day Of The Year | Dec 2010 | |
| Glee Cast |
| 9 | It's The Most Wonderful Time Of The Year | Dec 2013 | |
| City Harbor |
| 10 | It's The Most Wonderful Time Of The Year | Dec 2014 | |
| Michael W. Smith |