| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| December 1, 1999 | Thing | WEIGHT | B D H I | Trip to Aspen, Colorado | Yes |
| December 2, 1999 | PUPPET | P H C A | $25,000 | ||
| December 3, 1999 | SHAWL | H K P A | |||
| December 6, 1999 | Things | WAFFLES | P D M A | Grand piano | No |
| December 7, 1999 | On the Map | SANTIAGO | G M C A | $25,000 | Yes |
| December 8, 1999 | HARTFORD | M Y H U | Trip for 8 on United Airlines | ||
| December 9, 1999 | Thing | TOPIC | P D M A | Ford Explorer | No |
| December 10, 1999 | ZIPPER | M C D O | Grand piaon | ||
| December 13, 1999 | Phrase | ON THE BLINK | G H C O | Chrysler Sebring | No |
| December 14, 1999 | Thing | FIGURINE | C M B I | Jeep Cherokee | |
| December 15, 1999 | Phrase | RAZOR-THIN | C M P O | Chrysler Sebring | |
| December 16, 1999 | Thing | DOLPHIN | M C D A | ||
| December 17, 1999 | Event | HOCKEY GAME | C D G A | Sea Ray boat | Yes |
| December 20, 1999 | Phrase | I HAD A HUNCH | D P M A | Christmas stocking (Arbor snowboards, Yakima roof racks, and Chevrolet Tahoe) |
Yes |
| December 21, 1999 | Thing | WISHBONE | M P K O | Trip to Australia | |
| December 22, 1999 | SPRIG OF HOLLY | G C M O | Chevrolet Venture | ||
| December 23, 1999 | On the Map | FLAGSTAFF | C M H O | $25,000 | No |
| December 24, 1999 | Thing | OPAL RING | G C M I | ||
| December 27, 1999 | Around the House | PILLOW | P I W D | Route 66 trip | Yes |
| December 28, 1999 | On the Map | MICHIGAN | C D M A | Harley-Davidson Fat Boy | |
| December 29, 1999 | Phrase | TALK SHOP | F C B A | Restored 1965 Ford Mustang | No |
| December 30, 1999 | Thing | A NIFTY IDEA | H P C I | $25,000 | |
| December 31, 1999 | Person | BABY GIRL | G B I P | Yes | |
