| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| September 6, 1999 | Thing | BULLDOG | C D M O | $25,000 | No |
| September 7, 1999 | THICK HAIR | H M D A | Yes | ||
| September 8, 1999 | Phrase | IT BAFFLES ME | P H M O | Honda CRV | No |
| September 9, 1999 | Thing | NIGHTGOWN | H C P I | Jeep Wrangler + Kawasaki jet ski | |
| September 10, 1999 | Place | WORKPLACE | C H M A | ||
| September 13, 1999 | Place | HILLTOP | D B C O | Trip to Seattle + boat | No |
| September 14, 1999 | On the Map | HUNGARY | C P Y O | Trip to Canada + Mercedes | |
| September 15, 1999 | Phrase | I'M KEYED UP | D C M I | Trip to Vermont + Ford Mustang | |
| September 16, 1999 | BACK AND FORTH | D C M O | |||
| September 17, 1999 | Thing | GOLF CLUB | Trip to New Hampshire + Saab 9-3 | ||
| September 20, 1999 | Thing | DOOR PRIZE | F G C O | Donzi Pro-Line boat | No |
| September 21, 1999 | Person | MOVIEGOER | M C D A | ||
| September 22, 1999 | Thing | HUMIDITY | D C M O | Dodge Intrepid | |
| September 23, 1999 | NAPKIN | P G M I | Pair of Dodge Neons | Yes | |
| September 24, 1999 | FINGERTIP | D G P O | $25,000 | ||
| September 27, 1999 | Thing | BEAR HUG | C F D A | $25,000 | Yes |
| September 28, 1999 | People | OFFICIALS | M D B A | No | |
| September 29, 1999 | Thing | WHISPER | C D M A | Dodge Caravan | |
| September 30, 1999 | Person | BOYFRIEND | D G P A | Dodge Durango | Yes |
