| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 1, 2002 | Proper Name | JON BON JOVI | C D M A | $25,000 | No |
| May 2, 2002 | ELIJAH WOOD | H D M O | Yes | ||
| May 3, 2002 | Thing | A MOPED | C M D A | No | |
| May 6, 2002 | Thing | A GIFT CARD | W M K A | $25,000 | No |
| May 7, 2002 | Phrase | I'M HOPEFUL | D C M O | Yes | |
| May 8, 2002 | Around the House | BABY SHAMPOO | H D C A | No | |
| May 9, 2002 | Thing | BREAD DOUGH | M P G A | Toyota Sequoia | |
| May 10, 2002 | Things | WIND CHIMES | C D M I | $25,000 | Yes |
| May 13, 2002 | Thing | JUICY FRUIT | M C A P | $25,000 | No |
| May 14, 2002 | Phrase | I'M CURIOUS | M C D U | Yes | |
| May 15, 2002 | HANG TOUGH | H K M O | No | ||
| May 16, 2002 | HAPPY TO HELP | H P D O | Land Rover Freelander | Yes | |
| May 17, 2002 | Person | PARTYGOER | C M P I | No | |
| May 20, 2002 | Place | DUGOUT | C H M A | $100,000 | No |
| May 21, 2002 | Thing | GUACAMOLE DIP | G H B O | Chevrolet Blazer | |
| May 22, 2002 | A GOLF BAG | C D P A | $25,000 | Yes | |
| May 23, 2002 | Place | THE BANK | H C D I | No | |
| May 24, 2002 | Thing | HUMIDITY | C D M I | Chevrolet Corvette | No |
| May 27, 2002 | Thing | A HYPHEN | D M C A | $25,000 | No |
| May 28, 2002 | Event | FLAG DAY | C W D I | ||
| May 29, 2002 | Thing | A FISH BOWL | P H M A | Land Rover Discovery Series II | Yes |
| May 30, 2002 | Phrase | JUST FOR KICKS | J F K I | $25,000 | |
| May 31, 2002 | Thing | SHAVED ICE | P C M I | ||
