| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 1, 1990 | Person | CASANOVA | C P G A | $25,000 | Yes |
| May 2, 1990 | Place | MICHIGAN | M D P I | Precious metals | |
| May 3, 1990 | Thing | ANXIETY | C M P A | Pair of Chevrolets | No |
| May 4, 1990 | Phrase | UPS AND DOWNS | M P D O | Fred Joaillier women's gold watch | Yes |
| May 7, 1990 | Thing | PHONOGRAPH | C D G A | $25,000 | No |
| May 8, 1990 | BEAR MARKET | D C M A | Sport boat | Yes | |
| May 9, 1990 | Phrase | DEAD HEAT | F C D A | $25,000 | |
| May 10, 1990 | HOLY SMOKE | F C M A | Annuity | No | |
| May 11, 1990 | Thing | ICE AGE | C G M A | Trip to Switzerland | Yes |
| May 14, 1990 | Thing | PEPPERMINT GUM | C M D O | Annuity | Yes |
| May 15, 1990 | Event | CHECKMATE | C D M A | African safari | |
| May 16, 1990 | WEDDING NIGHT | G D W A | Necklace | ||
| May 17, 1990 | Things | LAMB CHOPS | M C D A | His-and-hers cars | No |
| May 18, 1990 | Phrase | CUT AND DRIED | G P M A | ||
| May 21, 1990 | Landmark | PIKES PEAK | C D P A | $30,000 annuity | Yes |
| May 22, 1990 | Place | BERMUDA | D B M A | $25,000 | |
| May 23, 1990 | Thing | HAYSTACK | D M P A | Sports car | No |
| May 24, 1990 | MASS MEDIA | M D P A | Jeep Cherokee | Yes | |
| May 25, 1990 | CHESS PAWN | B D M A | not revealed | No | |
| May 28, 1990 | Thing | MINIMUM WAGE | C H D I | Pinseeker golf clubs, trip to Orlando and Tampa, and Volkswagen Cabriolet | No |
| May 29, 1990 | Event | DRAG RACE | C D M I | Ruby and diamond ear clips | Yes |
| May 30, 1990 | BOXING MATCH | C D M O | Pinseeker golf clubs, trip to Orlando and Tampa, and Volkswagen Cabriolet | ||
| 31 May 1990 | Thing | SAGEBRUSH | G B M A | Four Seasons greenhouse | |
