| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 1, 2000 | Things | ANCHOVIES | C P G I | $25,000 from Amazon | Yes |
| May 2, 2000 | Phrase | KEEP IT HANDY | F H D A | $25,000 from USABancShares | |
| May 3, 2000 | Thing | POWERBOAT | P D H I | $25,000 from E-Trade | No |
| May 4, 2000 | Phrase | KICKING BACK | D C B A | $25,000 | |
| May 5, 2000 | Thing | HIGH FIVE | H M C A | Yes | |
| May 8, 2000 | Phrase | LICK YOUR LIPS | Y C P I | Mercedes-Benz ML320 | Yes |
| May 9, 2000 | Thing | CORNHUSK | B C M O | $25,000 from USABancShares | |
| May 10, 2000 | SWORDFISH | P C D A | $25,000 Sony Card | No | |
| May 11, 2000 | GIGGLE | M C H O | $25,000 | ||
| May 12, 2000 | Phrase | PAPER-THIN | M B C O | $25,000 from E-Trade | |
| May 15, 2000 | Thing | POLICY | C D M A | Sony entertainment package | No |
| May 16, 2000 | Phrase | FOR HIRE | H F C O | Trip to Hollywood | Yes |
| May 17, 2000 | Thing | A DEEP SIGH | C M P A | Sony entertainment package | No |
| May 18, 2000 | Phrase | WE HIT IT OFF | B V D I | $25,000 | |
| May 19, 2000 | Thing | BOOKMARK | B P H O | Lexus RX300 | |
| May 22, 2000 | Thing | FREIGHT CAR | C H M A | Mediterranean cruise | Yes |
| May 23, 2000 | Around the House | WHISK BROOM | C H B U | Dodge Durango | |
| May 24, 2000 | On the Map | WINNIPEG | Y C M I | Pair of Volkswagen New Beetles | |
| May 25, 2000 | Place | PIZZERIA | C D M A | $25,000 | No |
| May 26, 2000 | Event | A BRIEF CHAT | C H B A | Free airfare for a year | Yes |
| May 29, 2000 | Thing | HULA HOOP | D C M O | Annuity | No |
| May 30, 2000 | CHICKEN BROTH | H C B O | $25,000 | Yes | |
| May 31, 2000 | BEAUTY MARK | D M G O | $20,000 in Sacagawea dollars | No | |
