| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 3, 1999 | Place | HARBOR | P D G A | Sports fantasy package (Tickets to Flyers/76ers games, backstage dinner, cigars from Holt's Cigar, suite at First Union Center, autographed team merchandise, locker room tour) |
Yes |
| May 4, 1999 | Things | SOAPSUDS | C M D A | $25,000 | |
| May 5, 1999 | Phrase | GRAB A BITE | C M B A | Lexus RX300 | |
| May 6, 1999 | People | VIRGOS | B M C A | Porsche Boxster | No |
| May 7, 1999 | Phrase | THAT'S IFFY | M C P A | $25,000 | |
| May 10, 1999 | Thing | SCRAPBOOK | M C Y U | $25,000 | No |
| May 11, 1999 | TUBE TOP | K W B A | Yes | ||
| May 12, 1999 | Phrase | I'M STUFFED | M P D I | Jeep Wrangler | No |
| May 13, 1999 | Thing | FISH STICK | M D P A | Mercury Cougar | |
| May 14, 1999 | Phrase | SKIP IT | M D Y A | Jeep Wrangler | |
| May 17, 1999 | Phrase | FINE WITH ME | M C P O | Chevrolet Corvette | No |
| May 18, 1999 | IN HIGH GEAR | D M H I | Land Rover | ||
| May 19, 1999 | Thing | BAGGAGE | C D H I | Trip to Hollywood | |
| May 20, 1999 | On the Map | KENYA | K Y G A | Land Rover | Yes |
| May 21, 1999 | Thing | FLOPPY DISK | F W V A | Home theater package | No |
| May 24, 1999 | Thing | YACHT | C M G A | Chevrolet Camaro | No |
| May 25, 1999 | TULIP | C D P U | Ford Mustang | Yes | |
| May 26, 1999 | MOTORBIKE | M D P A | $25,000 | No | |
| May 27, 1999 | Phrase | BY DESIGN | M Y B O | Chevrolet Camaro | |
| May 28, 1999 | Place | WHARF | M P C A | Trip to Bora Bora | |
| May 31, 1999 | Phrase | ON A WHIM | P C M I | Trip to France | No |
