| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| January 8, 1990 | Person | CHOIRBOY | D C M A | Toyota Celica | No |
| January 9, 1990 | Thing | PIE A LA MODE | C P M A | Sport boat | Yes |
| January 10, 1990 | Place | FAMILY ROOM | C D H O | Cadillac Eldorado | |
| January 11, 1990 | Thing | GIBBERISH | H M C A | His-and-hers Rolex diamond watches | No |
| January 12, 1990 | People | CAVALCADE | C D M O | $25,000 | Yes |
| January 15, 1990 | People | CLIQUE | D C M I | Precious metals package | Yes |
| January 16, 1990 | Title | WALK ON BY | W D M O | Annuity | |
| January 17, 1990 | Phrase | GOOD LUCK | C M P O | Toyota Cressida | |
| January 18, 1990 | Thing | INSOMNIA | M D P I | $25,000 | |
| January 19, 1990 | TEAMWORK | D M C A | Chevrolet Astro | ||
| January 22, 1990 | Person | VENDOR | D V C O | Jewelry package | Yes |
| January 23, 1990 | Thing | CLAY PIGEON | B C H A | Chevrolet | No |
| January 24, 1990 | Things | DIAPERS | B C D A | Champion Telstar motor home | Yes |
| January 25, 1990 | Place | HAYLOFT | C H D A | Trip to Switzerland | No |
| January 26, 1990 | Phrase | MAKE A MUSCLE | G I M H | $25,000 | Yes |
| January 29, 1990 | Thing | BEAUTY TIP | M H C A | $25,000 | No |
| January 30, 1990 | HEADACHE | D P M A | $30,000 savings bonds | Yes | |
| January 31, 1990 | Phrase | ALL GROWN-UP | P D C A | Tour of Europe | |
