| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| November 1, 1999 | Event | POKER GAME | K C D A | Trip to Laguna Beach + Mazda Miata | No |
| November 2, 1999 | Things | BICEPS | C M P O | Trip to Palm Desert + Chevrolet Camaro | Yes |
| November 3, 1999 | Thing | FIG TREE | K M D A | Trip to Beverly Hills + Ford Explorer | |
| November 4, 1999 | Phrase | TAPERING OFF | D M C A | $25,000 | |
| November 5, 1999 | On the Map | CAMBRIDGE | C D M A | Trip to Laguna Beach + Mazda Miata | No |
| November 8, 1999 | People | FAMILY | C M P O | Audi TT | Yes |
| November 9, 1999 | Phrase | KEEP IT BRIEF | K P G I | $25,000 | |
| November 10, 1999 | SHOW ME HOW | M H P O | Land Rover | ||
| November 11, 1999 | Thing | GUMBALL | B P G A | Chrysler 300M | |
| November 12, 1999 | WOOL CAP | D G C A | Lexus RX300 | ||
| November 15, 1999 | Phrase | TAKE FIVE | M D H A | Tour of Titanic wreckage | No |
| November 16, 1999 | Place | BOROUGH | D P C A | Sony electronics package | |
| November 17, 1999 | Around the House | SOAP DISH | P H D I | Pair of Volkswagen New Beetles | Yes |
| November 18, 1999 | Thing | TAFFY | M H C A | Sony electronics package | No |
| November 19, 1999 | Things | SPARK PLUGS | H F D O | Pair of Chrysler Sebrings | |
| November 22, 1999 | Thing | HOUSE KEY | P D B O | Trip to NBA All-Star Game + Buick Regal GS | Yes |
| November 23, 1999 | Phrase | PLAY FAIR | D M I G | $25,000 | |
| November 24, 1999 | People | BUDDIES | C W M I | Chevrolet Silverado | No |
| November 25, 1999 | PILGRIMS | D K P I | Chevrolet Trailblazer | Yes | |
| November 26, 1999 | Thing | SPINACH | G D M O | Trip to Japan | No |
| November 29, 1999 | Event | GRIDLOCK | C G M A | Trip to Canada + Chevrolet Camaro | Yes |
| November 30, 1999 | On the Map | FRANKFURT | F K O C | Trip to Lake Tahoe + Chevrolet Tahoe | |
