| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| January 1, 1999 | Thing | ICEBERG | Y D M A | $25,000 | No |
| January 4, 1999 | Place | BANGKOK | B C H A | Trip to Miami + boat | No |
| January 5, 1999 | Thing | RED FOX | C D G A | ||
| January 6, 1999 | FLUID | B P C A | Trip to Palm Beach + convertible | ||
| January 7, 1999 | People | GOSPEL CHOIR | C D M A | Trip to Orlando + Jeep | Yes |
| January 8, 1999 | Thing | ROWBOAT | H C M A | $25,000 | No |
| January 11, 1999 | Place | FACTORY | C P D A | GMC van | Yes |
| January 12, 1999 | Person | WIFE | B C G O | Land Rover | No |
| January 13, 1999 | Thing | GOOD ADVICE | C D M O | Africa trip | Yes |
| January 14, 1999 | Phrase | THUMBS UP | M D G A | $25,000 | No |
| January 15, 1999 | SHRUG IT OFF | H D F I | Land Rover | Yes | |
| January 18, 1999 | Place | PHARMACY | D C M A | Trip to Oregon + Chrysler Town & Country | Yes |
| January 19, 1999 | Phrase | THINK FAST | P G C A | Trip to Coronado + sailboat | No |
| January 20, 1999 | Thing | ALBUM | G P M O | Trip to Laguna Beach + convertible | |
| January 21, 1999 | Phrase | I'M FULL | F D M I | Trip to Santa Barbara + boat | Yes |
| January 22, 1999 | Place | CITY | F M B A | $25,000 | No |
| January 25, 1999 | Thing | TAILPIPE | G B H A | Trip to Utah + Chevrolet Silverado | No |
| January 26, 1999 | Phrase | ROUGHING IT | D M H I | $25,000 | |
| January 27, 1999 | Person | KICKER | C D M A | ||
| January 28, 1999 | Place | SUBURB | C D P A | Chevrolet Camaro | |
| January 29, 1999 | Things | BAGGIES | C D H A | Trip to Utah + Chevrolet Silverado | |
