| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| October 1, 2008 | Place | PHOTO LAB | M D C A | $45,000 | No |
| October 2, 2008 | Phrase | SHOP AROUND | C B H A P | $30,000 | Yes |
| October 3, 2008 | Thing | OATH OF OFFICE | F M B O | $25,000 | No |
| October 6, 2008 | Thing | SPARK PLUG | B H C I | $100,000 | No |
| October 7, 2008 | Place | EXIT RAMP | M C D O | $40,000 | Yes |
| October 8, 2008 | Thing | CHARISMA | H D C A | $50,000 | |
| October 9, 2008 | A LOUD VOICE | G C M A | $30,000 | No | |
| October 10, 2008 | Proper Name | BOB DYLAN | C D B O | $35,000 | Yes |
| October 13, 2008 | Things | JEAN SHORTS | C H D O | $30,000 | Yes |
| October 14, 2008 | Around the House | LEAKY FAUCET | C D M A | $1,000,000 | |
| October 15, 2008 | Phrase | LIVING ABROAD | D M P A C | $25,000 | No |
| October 16, 2008 | Phrase | FIGHT THE URGE | H D C O | $30,000 | |
| October 17, 2008 | Place | FOOTPATH | P C G A | Yes | |
| 20 October 20, 2008 | Thing | UPHILL CLIMB | C M P A | $30,000 | No |
| October 21, 2008 | BLAZING SPEED | H C P A | Yes | ||
| October 22, 2008 | DAILY DIARY | M C G I | $100,000 | No | |
| October 23, 2008 | Living Thing | INCHWORM | D M C O | $30,000 | |
| October 24, 2008 | Thing | DEBIT CARD | C D M A | $100,000 | Yes |
| October 27, 2008 | Phrase | PLAYING A HUNCH | P G M A F | $25,000 | No |
| October 28, 2008 | Event | HEAVY DOWNPOUR | D M C O | Mitsubishi Eclipse Spyder | |
| October 29, 2008 | Thing | HIGH FIVE | D M C O | ||
| October 30, 2008 | Person | VISIONARY | Y I G H | $25,000 | Yes |
| October 31, 2008 | CRYBABY | P C D A | Mitsubishi Eclipse Spyder | No | |
