| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| February 1, 1999 | Event | AUCTION | C B D A | $25,000 | Yes |
| February 2, 1999 | People | BOYS | M G H A | Trip to New Orleans + Ford Mustang | No |
| February 3, 1999 | Thing | SPATULA | P K C A | Trip to Germany + Volkswagen New Beetle | Yes |
| February 4, 1999 | Phrase | BIT BY BIT | B C M A | $25,000 | |
| February 5, 1999 | Thing | WHITE GOLD | M D C A | No | |
| February 8, 1999 | Phrase | OFF THE CUFF | C P M O | $25,000 | No |
| February 9, 1999 | Things | COMB & BRUSH | C P D A | London + Infiniti I30 | |
| February 10, 1999 | Thing | GOWN | C D M O | Trip to French and Italian Riviera | |
| February 11, 1999 | DISPLAY | C W D O | Trip for 4 to Spain | ||
| February 12, 1999 | Things | HIPS | C P M I | London + Infiniti I30 | Yes |
| February 15, 1999 | Things | GUPPIES | D C M A | Chrysler Town & Country | No |
| February 16, 1999 | Thing | STICKPIN | H A F P | Chrysler Sebring | |
| February 17, 1999 | BLUEBIRD | B F G O | Chrysler Town & Country | Yes | |
| February 18, 1999 | CAKE MIX | C D M A | Chrysler Sebring | No | |
| February 19, 1999 | FISH BAIT | P C M O | Mercedes-Benz SLK | ||
| February 22, 1999 | Phrase | I'M IN SHOCK | D M H O | Speedboat | Yes |
| February 23, 1999 | Thing | SOUP MUG | K P M O | Jeep | No |
| February 24, 1999 | Phrase | FROZEN STIFF | C D M A | ||
| February 25, 1999 | Thing | RHUBARB PIE | B M C O | $25,000 | Yes |
| February 26, 1999 | FABRIC | C D M A | Mazda Miata | ||
