| 100% | TWELFTH | 7 | "On the ___ day of Christmas ..." (start of a holiday song's last verse) |
| 54% | TWELFTH | 7 | In song, the last day of Christmas |
| 54% | SLEEPINGIN | 10 | Getting a late start on the day |
| 52% | ILUVU | 5 | Start of the song title in the 25 Across clue, but imagine it on Valentine's Day candy |
| 51% | HANUKKAH | 8 | Jewish holiday starting on the 25th day of Kislev |
| 50% | MEXICO | 6 | Country just south of the US ... or the title of a song on Carrie Underwood's latest album |
| 50% | GEESE | 5 | Birds given on the sixth day of Christmas, in song |
| 50% | DRUMMERS | 8 | Gifts given on the 12th day of Christmas, in song |
| 50% | CHASER | 6 | Drink that follows a hard-liquor shot ... or the title of a song on Carrie Underwood's latest album |
| 49% | SANTASHADANEASYSEASON | 21 | Start of a holiday verse |
| 49% | OCOME | 5 | Start of a Christmas song |
| 49% | HOME | 4 | "___ on the Range," western folk song that's also the Kansas state song fitting for a "National Day of the Cowboy" playlist |
| 49% | CHURCHBELLS | 11 | Chimes that beckon parishioners on Sunday morning ... or the title of a song on Carrie Underwood's latest album: 2 wds. |
| 48% | TURTLEDOVE | 10 | Old World bird with a brown plumage and speckled wings associated with song The Twelve Days of Christmas |
| 48% | SYNE | 4 | Last word of a holiday song title |
| 48% | EAGLES | 6 | Band that released a cover version of the holiday song "Please Come Home for Christmas" |
| 47% | DAWNRAID | 8 | Huge stock purchase at the start of a day's trading |
| 47% | OHIINTENDTOGOMYROUNDS | 21 | Start of a Christmas verse |
| 47% | HANGUPYOURSTOCKINGSDO | 21 | Start of a Christmas verse |
| 47% | DANCING | 7 | The ladies were doing this on 9th day of Christmas |
| 47% | PEAR | 4 | On the first day of Christmas, your true love may send you a partridge in this "poached fruit" tree |
| 47% | ABC | 3 | Letters at the start of a preschool song |
| 46% | ONCE | 4 | (1/7) "___ a year, during the crisp days of late November, families eagerly prepare for a special holiday." |
| 46% | SOMEPEOPLELIKETOICEIT | 21 | Start of a verse about holiday fruitcake |
| 46% | QUESERA | 7 | Start of a Doris Day song title |
| 46% | INTROIT | 7 | Song at the start of a church service |
| 46% | BLANKSPACE | 10 | "1989 (Taylor's Version)" song about the start of a potentially temporary relationship (2 wds.) |
| 45% | SOLARARC | 8 | The progression of the sun on a given day |
| 45% | GEESE | 5 | "On the sixth day of Christmas, my true love sent to me, six ___ a-laying..." |
| 45% | SWANS | 5 | "On the seventh day of Christmas, my true love sent to me, seven ___ a-swimming" |