| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| October 2, 1989 | People | SQUADRON | C H M O | Pin from Van Cleef and Arpels | Yes |
| October 3, 1989 | Event | LUNCH BREAK | C D M A | Cadillac Seville | |
| October 4, 1989 | Phrase | HIGH AND DRY | D C M A | $25,000 | |
| October 5, 1989 | Place | MEZZANINE | A C M D | Toyota Supra | No |
| October 6, 1989 | Thing | BUMPY ROAD | B C G A | ||
| October 9, 1989 | Thing | CLIFF HANGER | B D G A | Pair of gold watches from Van Cleef and Arpels |
No |
| October 10, 1989 | LIBRARY BOOK | C D G O | Touring coach | ||
| October 11, 1989 | Phrase | HORSEPLAY | F D M O | BMW | |
| October 12, 1989 | TAKE CHARGE | H C D A | Trip to Jamaica | Yes | |
| October 13, 1989 | Person | MISSIONARY | C D M A | Pair of gold watches from Van Cleef and Arpels |
|
| October 16, 1989 | Person | MONARCH | P D M I | $25,000 | No |
| October 17, 1989 | Thing | WHIPLASH | C D M A | ||
| October 18, 1989 | Person | JACKIE MASON | M C D A | Pair of gold and diamond necklaces | Yes |
| October 19, 1989 | Event | CLAMBAKE | M P C O | China and Japan cruise | |
| October 20, 1989 | Place | DOG HOUSE | C D M A | Avanti convertible | |
| October 23, 1989 | Thing | QUOTATION | C M P A | Annuity | No |
| October 24, 1989 | Event | BLOCK PARTY | P Y C A | Born Free motor coach | Yes |
| October 25, 1989 | Thing | JACK OF CLUBS | C D M A | $25,000 | No |
| October 26, 1989 | Place | COMMONWEALTH | C D M I | 18-karat watches from Van Cleef and Arpels |
Yes |
| October 27, 1989 | Thing | WHIPPED CREAM | D M W A | $40,000 annuity | |
| October 30, 1989 | Thing | BLACKBOARD | C F D I | Home electronics package | Yes |
| October 31, 1989 | PIECE OF CAKE | C D M O | European tour | ||
