| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| May 1, 1989 | Person | QUICK STUDY | D C P A | $25,000 | No |
| May 2, 1989 | |||||
| May 3, 1989 | Nickname | HOT LIPS | C G D O | Toyota Cressida and Toyota Supra | Yes |
| May 4, 1989 | Thing | LOGIC | C H P A | $25,000 | No |
| May 5, 1989 | BANK OF AMERICA | B C P A | Yes | ||
| May 8, 1989 | Thing | CHIPMUNK | C G M A | Buick Century and Buick Park Avenue | No |
| May 9, 1989 | GRAB BAG | B C D A | $25,000 | Yes | |
| May 10, 1989 | Phrase | A HIT OR A MISS | H M Z A | ||
| May 11, 1989 | Thing | PIECE OF PIE | C D F O | ||
| May 12, 1989 | Person | WILLIE MAYS | C D B A | ||
| May 15, 1989 | Things | POLKA DOTS | C D H A | $25,000 | Yes |
| May 16, 1989 | Phrase | DAYDREAMING | H D C A | BMW 325i | No |
| May 17, 1989 | |||||
| May 18, 1989 | Phrase | TUG OF WAR | F C D O | $25,000 | Yes |
| May 19, 1989 | People | ROCK BAND | C D K O | Pair of Ford E-Series vans | |
| May 22, 1989 | |||||
| May 23, 1989 | Thing | CIVILIZATION | C D M O | $25,000 | No |
| May 24, 1989 | |||||
| May 25, 1989 | |||||
| May 26, 1989 | |||||
| May 29, 1989 | |||||
| May 30, 1989 | |||||
| May 31, 1989 | Thing | STICK OF GUM | C D M A | $25,000 | Yes |
