| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| December 1, 2000 | On the Map | HAITI | D G H A | Chevrolet Blazer | Yes |
| December 4, 2000 | Phrase | WHAT'S COOKING? | H G C A | Jeep Wrangler | No |
| December 5, 2000 | Event | JOB FAIR | H C D O | Saab convertible | |
| December 6, 2000 | Thing | TABBY CAT | C H M A | $25,000 | Yes |
| December 7, 2000 | TOOTHPICK | M C H A | Jeep Wrangler | ||
| December 8, 2000 | People | HUNGARIANS | C G D I | Trip to Grenada + West Wight Potter sailboat | |
| December 11, 2000 | Phrase | BRIDGE THE GAP | C D H I | Indian Scout motorcycle | No |
| December 12, 2000 | Around the House | SCRUB BRUSH | H C P U | Route 66 tour | Yes |
| December 13, 2000 | Thing | POUND CAKE | I B C D | Indian Scout motorcycle | |
| December 14, 2000 | On the Map | NAIROBI | M D C A | Chevrolet Camaro | |
| December 15, 2000 | Phrase | I'M OFF DUTY | D B W I | $25,000 | No |
| December 18, 2000 | Phrase | HE TIPPED ME OFF | M W H A | Asian cruise | No |
| December 19, 2000 | Thing | PERFUME | C M P O | Mazda Miata | Yes |
| December 20, 2000 | Event | FOGGY NIGHT | B C D A | $25,000 | No |
| December 21, 2000 | Show Biz | HIGH-WIRE ACT | C D M A | ||
| December 22, 2000 | Thing | KEY WORD | W P D O | Trip to Hong Kong + Honda | |
| December 25, 2000 | Thing | WHITE DOVE | G M P A | Trip to the Caribbean | No |
| December 26, 2000 | Things | BABY CHICKS | D P M A | ||
| December 27, 2000 | Phrase | EBB AND FLOW | D C M O | A year of travel | |
| December 28, 2000 | Person | CHURCHGOER | B C D A | Toyota MR2 Spyder | |
| December 29, 2000 | Thing | PIPPIN APPLE | C D M I | ||
