| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| October 1, 1999 | Things | WEEKNIGHTS | H C M A | Dodge Caravan | No |
| October 4, 1999 | Event | A WEEK OFF | D H P A | Trip to Lake Havasu City + Hunter 240 sailboat | No |
| October 5, 1999 | Thing | FIRE TRUCK | F C K I | Yes | |
| October 6, 1999 | Person | COLLEAGUE | B M P A | Trip to Oregon + Chevrolet Venture | |
| October 7, 1999 | Event | LUNCH HOUR | D M H A | Gold and silver package | |
| October 8, 1999 | On the Map | FAIRBANKS | C D M A | $25,000 | No |
| October 11, 1999 | Phrase | HOT AND SPICY | D C M A | Trip to Germany + Infiniti G20 | No |
| October 12, 1999 | Thing | GIFT TAG | M G H A | Trip to London + Infiniti I30L | Yes |
| October 13, 1999 | On the Map | BOLIVIA | C M D O | Trip to French & Italian Riviera | |
| October 14, 1999 | Thing | BIG TOE | B W M I | $25,000 | |
| October 15, 1999 | Phrase | SHAKE IT UP | M C P A | Trip to Spain | |
| October 18, 1999 | Phrase | DON'T BE SHY | D M Y A | Asian cruise | No |
| October 19, 1999 | On the Map | MANITOBA | B D G A | $25,000 | |
| October 20, 1999 | Event | A BRISK WALK | C H G A | Trip to Hong Kong + Honda Prelude | Yes |
| October 21, 1999 | On the Map | AUGUSTA | D M C A | Trip to Shanghai + Acura CL | No |
| October 22, 1999 | Things | PISTACHIOS | C D M A | Asian cruise | Yes |
| October 25, 1999 | Phrase | NO JOKE | B G H O | $25,000 | Yes |
| October 26, 1999 | Event | FAMILY TRIP | P D M I | Trip to Transylvania | |
| October 27, 1999 | Person | GOALIE | M C D O | $25,000 | No |
| October 28, 1999 | On the Map | WICHITA | C D M A | Tour of Frankenstein's castle | |
| October 29, 1999 | Fictional Character | WARLOCK | M D G A | Chevrolet Silverado | |
