| DATE | CATEGORY | PUZZLE | LETTERS | PRIZE | WIN |
| June 2, 2008 | People | TWIN BOYS | M D P O | $35,000 | No |
| June 3, 2008 | Thing | DIVING MASK | H D M I C | $30,000 | |
| June 4, 2008 | OFFICIAL FAN CLUB | C A M P | Volvo C70 | ||
| June 5, 2008 | People | IOWANS | M H C A | $30,000 | |
| June 6, 2008 | Phrase | I MADE A VOW | M D C I B | Yes |
