| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| September 7, 1998 | People | FLIGHT CREW | D A M B | $25,000 | Yes |
| September 8, 1998 | Thing | PAPERWORK | D M C A | Dodge Ram | No |
| September 9, 1998 | Things | GUMDROPS | D M P O | Boston Whaler boat | Yes |
| September 10, 1998 | Occupation | BAKER | C M D I | Dodge Ram | No |
| September 11, 1998 | Thing | HARMONICA | Chevrolet Corvette | ||
| September 14, 1998 | Thing | FORK | C F K O | Dodge Durango, food from Basket of Pittsburgh, and Grand Hall barbecue grill |
Yes |
| September 15, 1998 | Phrase | DON'T HOLD BACK | C H P A | Dodge Caravan | No |
| September 16, 1998 | Place | LOBBY | C D M O | Yes | |
| September 17, 1998 | Thing | GIRAFFE | D C P A | Nissan 200ZX | |
| September 18, 1998 | GUITAR | M P C O | Boat (type not stated in-show) | No | |
| September 21, 1998 | Place | SUSHI BAR | H B C A | Trip to Plymouth, Massachusetts + Mercedes-Benz C230 | Yes |
| September 22, 1998 | PRAGUE | C D M A | $25,000 | ||
| September 23, 1998 | Thing | MARIGOLD | Trip to Palm Desert + Volkswagen Cabrio | ||
| September 24, 1998 | Phrase | I DREW A BLANK | M G K A | Trip to Martha's Vineyard + sailboat | |
| September 25, 1998 | Thing | TROPHY | G D M A | $25,000 | No |
| September 28, 1998 | Phrase | IN THE BUFF | D M A C | Trips to Portofino + Monte Carlo | No |
| September 29, 1998 | Place | BALCONY | C H G A | Yes | |
| September 30, 1998 | Thing | PENGUIN | P G W I | Saab 9-5 | |
