| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| October 2, 2000 | Thing | BIG DIPPER | C M P A | Queen Elizabeth II cruise | No |
| October 3, 2000 | Phrase | THAW OUT | H M P A | Chevrolet Blazer | |
| October 4, 2000 | LOW IN FAT | C D M O | Chevrolet Camaro | ||
| October 5, 2000 | Thing | CHECK STUB | P D M A | $25,000 | |
| October 6, 2000 | Phrase | HIT THE JACKPOT | C H P O | Trip to Canada + West Wight Potter 19 sailboat | Yes |
| October 9, 2000 | Show Biz | MAGICIAN | M C D A | Lexus RX300 | Yes |
| October 10, 2000 | On the Map | BOISE | B H M O | $20,000 in Sacagawea dollars | |
| October 11, 2000 | Around the House | CUPBOARD | M D H A | Annuity | No |
| October 12, 2000 | SKYLIGHT | D B C O | $25,000 | ||
| October 13, 2000 | Phrase | LAUGH IT OFF | M C H A | Annuity | |
| October 16, 2000 | Around the House | PINE HUTCH | C D M A | Trips to Beverly Hills and New York City | No |
| October 17, 2000 | On the Map | GEORGIA | C B D A | Audi A4 | |
| October 18, 2000 | Phrase | TAKE FLIGHT | M H P I | Trips to Beverly Hills and New York City | |
| October 19, 2000 | Thing | HALIBUT | H G F I | Jeep Cherokee | |
| October 20, 2000 | Around the House | RECIPE BOX | F C M A | Infiniti G20 | |
| October 23, 2000 | Phrase | WAFER-THIN | D H C O | Toyota 4Runner | No |
| October 24, 2000 | People | BOLIVIANS | C D I M | Donzi 22ZX speedboat | |
| October 25, 2000 | Thing | WAGON | B D M A | Toyota 4Runner | |
| October 26, 2000 | Person | RABBI | D M B A | Donzi 22ZX speedboat | Yes |
| October 27, 2000 | Phrase | OH MY GOSH | C B H A | Volkswagen Jetta + trip to Martha's Vineyard | |
| October 30, 2000 | Thing | HAIRPIN | C D M A | Mitsubishi Eclipse Spider | Yes |
| October 31, 2000 | BLACKBIRD | C H M I | $25,000 | No | |
