| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| January 3, 2000 | Thing | CARGO SHIP | M D H A | Jeep Cherokee | No |
| January 4, 2000 | Around the House | AREA RUG | D K P I | Kawasaki jet skis | |
| January 5, 2000 | Place | PLAZA | C D P A | Ford Expedition | Yes |
| January 6, 2000 | Thing | GLOBE | C M P A | $25,000 | No |
| January 7, 2000 | Phrase | SILKY-SOFT | H P C O | ||
| January 10, 2000 | Thing | BEEHIVE | C D B A | $20,000 online shopping spree from CitiPlaza | No |
| January 11, 2000 | CHOP SUEY | H M P O | |||
| January 12, 2000 | Things | CUFFS | M P H A | Annuity | |
| January 13, 2000 | Event | BLIZZARD | J D M I | $20,000 online shopping spree from CitiPlaza | Yes |
| January 14, 2000 | Thing | WINDPIPE | D M P O | $20,000 in Sacagawea dollars | No |
| January 17, 2000 | Place | LIBRARY | D Y C O | $25,000 | No |
| January 18, 2000 | Thing | HORIZON | C H M I | Winnebago | |
| January 19, 2000 | FLAVOR | P M H A | $25,000 | ||
| January 20, 2000 | SAPPHIRE | G F P I | Indian Chief motorcycle | Yes | |
| January 21, 2000 | Fictional Character | PORKY PIG | C D P A | Winnebago | |
| January 24, 2000 | Person | HALFBACK | D H P A | Chevrolet Tahoe | No |
| January 25, 2000 | Event | RUBDOWN | P M C I | Golfing adventure | |
| January 26, 2000 | Thing | SAUSAGE | C H M I | Chevrolet Tahoe | |
| January 27,, 2000 | Event | SHUTOUT | P C H O | Chevrolet Camaro | Yes |
| January 28, 2000 | Phrase | JOIN HANDS | D G C A | Golfing adventure | No |
| January 31, 2000 | Thing | OPINION | C D P O | Ford Mustang | Yes |
