| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| January 1, 2014 | Things | HEADPHONES | D C P O | Chevrolet Camaro | Yes |
| January 2, 2014 | Food & Drink | CHOWDER | C D F I | $30,000 | |
| January 3, 2014 | Phrase | NICE JOB | C D M A | No | |
| 6 January 2014 | Things | PROBING QUESTIONS | G C P I | $30,000 | No |
| January 7, 2014 | Thing | BEDROCK | C H D I | $35,000 | Yes |
| January 8, 2014 | Person | COMPANY BIGWIG | C P H O | $30,000 | No |
| January 9, 2014 | Thing | EXHIBITION | C D H O | ||
| January 10, 2014 | Phrase | I'M ON THE LOOKOUT | M H B I P | ||
| January 13, 2014 | Phrase | QUITE A PAIR | H G C A | $30,000 | No |
| January 14, 2014 | Thing | YOUR HOMEWORK | Y C D O | Yes | |
| January 15, 2014 | BEVELED FRAME | G B H O | No | ||
| January 16, 2014 | HYBRID VEHICLE | C D H O | Yes | ||
| January 17, 2014 | UPLIFTING SPEECH | C D H A | $40,000 | No | |
| January 20, 2014 | Person | JOVIAL HOST | C M B A | $30,000 | No |
| January 21, 2014 | Phrase | JUST GOOGLE IT | D P M I | Volkswagen Beetle convertible | |
| January 22, 2014 | ECONOMY SIZE | M C D O | $30,000 | Yes | |
| January 23, 2014 | Thing | FLUFFY WOOL | D G C O | No | |
| January 24, 2014 | PINK FEATHER BOA | H M P O | $45,000 | ||
| January 27, 2014 | People | A CAPPELLA GROUP | G M H O D | $30,000 | No |
| January 28, 2014 | Things | WITTY PUNS | H F P I | $40,000 | |
| January 29, 2014 | JUNE JULY AND AUGUST | C M B A | $35,000 | ||
| January 30, 2014 | Thing | GUTSY CHOICE | G C H O | $30,000 | Yes |
| January 31, 2014 | Person | MAJORITY OWNER | M D P I | No | |
