| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| October 1, 1996 | Thing | IMAGE | C D M A | Trip to London | No |
| October 2, 1996 | JADE | C D M O | Range Rover | Yes | |
| October 3, 1996 | PROVERB | B M D I | Pearl necklace | ||
| October 4, 1996 | SYMBOL | C M P A | $25,000 | ||
| October 7, 1996 | Thing | VALVE | D P C A | Gold and silver package | No |
| October 8, 1996 | INDEX | D C P A | Trip to Rio de Janeiro | ||
| October 9, 1996 | Event | COLUMBUS DAY | D C M O | $25,000 | Yes |
| October 10, 1996 | Person | WIFE | C D M A | Trip to Rio de Janeiro | No |
| October 11, 1996 | Thing | CAPTION | D M G O | Trip to Mexico + Chevrolet Blazer | Yes |
| October 14, 1996 | Thing | DEVICE | C P M A | $25,000 | No |
| October 15, 1996 | RADISH | M D W O | Saab 900SE Turbo | Yes | |
| October 16, 1996 | Proper Name | MOZART | C M D A | $25,000 | |
| October 17, 1996 | Person | JOGGER | D M C O | Trip to France | No |
| October 18, 1996 | Thing | PURRING CAT | M G C A | Trip to Italy | Yes |
| October 21, 1996 | People | CHORUS | D M C A | $25,000 | No |
| October 22, 1996 | Thing | ADJECTIVE | C P D A | Yes | |
| October 23, 1996 | PIGEON | M D C O | Trip to Bora Bora | ||
| October 24, 1996 | SOFA | H M D A | Asian cruise | ||
| October 25, 1996 | Phrase | BUCKLE UP | D H C I | Ford Mustang | |
| October 28, 1996 | Thing | DIARY | H G P A | Hunter sailboat | No |
| October 29, 1996 | TOPIC | C M H A | Chevrolet S10 | Yes | |
| October 30, 1996 | GOULASH | D Y G A | Hunter sailboat | ||
| October 31, 1996 | WHISK BROOM | D C P I | Chevrolet Cavalier | No | |
