| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 1, 2001 | Living Thing | MARIGOLD | O M C H | Toyota 4Runner | Yes |
| May 2, 2001 | Phrase | I'M HIP TO IT | M C B I | $25,000 | |
| May 3, 2001 | FLIP THE SWITCH | P H M A | Mercedes ML320 | No | |
| May 4, 2001 | Thing | CHECKBOOK | M F B O | Toyota MR2 Spyder | |
| May 7, 2001 | Living Thing | PORPOISE | C P O M | Toyota 4Runner | Yes |
| May 8, 2001 | Thing | FERRYBOAT | C D H I | $25,000 | No |
| May 9, 2001 | Phrase | I'M VERY PICKY | M P C I | Audi A4 | Yes |
| May 10, 2001 | Things | JUMBO EGGS | C M P A | Toyota Land Cruiser | No |
| May 11, 2001 | Thing | CHILI | M P K A | Porsche Boxster | |
| May 14, 2001 | Thing | FRUIT JUICE | C P M I | Pair of Toyota MR2 Spyders | No |
| May 15, 2001 | SAXOPHONE | B C D A | 1,000,000 Advantage Miles from American Airlines | ||
| May 16, 2001 | BOX LUNCH | C P M A | Pair of Toyota MR2 Spyders | Yes | |
| May 17, 2001 | Classic TV | GILLIGAN | C P D A | Pair of Toyota Tacomas | |
| May 18, 2001 | Phrase | JAZZ IT UP | P M K U | 1,000,000 Advantage Miles from American Airlines | No |
| May 21, 2001 | People | YUPPIES | D C K A | Mazda Miata | No |
| May 22, 2001 | Around the House | PHONE JACK | C M G A | BMW 330i | |
| May 23, 2001 | Phrase | I'M FAMISHED | C D H I | Infiniti G20 | |
| May 24, 2001 | HIGH JINKS | C P D I | Lexus SUV | ||
| May 25, 2001 | IN VOGUE | C P B I | Infiniti G20 | ||
| May 28, 2001 | Thing | SYRUP | M F G A | Porsche Boxster | No |
| May 29, 2001 | Show Biz | JUGGLER | C G D O | Yes | |
| May 30, 2001 | Phrase | I APOLOGIZE | G C M A | Jeep Wrangler | No |
| May 31, 2001 | Place | BAKERY | Y B C A | $25,000 | Yes |
