- In general (although to a far lesser extent than the below), anyone who won all three trips in the Getaway era.
- In general, any "true daily double" wins on a Crossword Extra.
- In general, anybody who won $10,000 or more, especially before the Bonus Round. Neither was easy.
- September 17, 2007: John Beck, former Jeopardy! champion, wins $10,300 and all three trips (Palm Springs, Las Vegas, and Cabo San Lucas).
- October 16, 2007: Bruce Haights wins $11,550 plus trips to Lake Tahoe and Las Vegas (despite losing the bonus round).
- November 18, 2007: Stuart Minskoff wins $10,300 plus an Xbox 360 gaming package and a trip to Jamaica.
- November 23, 2007: Ed Young wins $12,800 plus an Xbox 360 gaming package and a trip to Cabo San Lucas. (One of his opponents was Theresa Carey, daughter of MacDonald Carey.)
- February 15, 2008: Thad Novak becomes what appears to be the show's biggest winner, getting $17,100 plus a trip to Nuevo Vallarta.
- February 21, 2008: Dan Rowley wins $13,000 plus a trip to Cancun.
- March 5, 2008: David Whitley wins $13,100 plus trips to San Francisco and Antigua. Note that this and Rowley's win were during the "$2,000 bonus" period.
- March 13, 2008: Vince Foley wins $12,100 plus a trip to Cancun.
- March 18, 2008: Brendan Pimper wins $12,100 plus trips to Phoenix and Antigua, beating out Bob House (who had dominated the game until the very last clue).
- July 4, 2008: Eddee Kolos wins $12,800 and all three trips (La Jolla, Palm Springs, and St. Lucia).
Awesome / Merv Griffin's Crosswords
Even Crosswords, as broken as it was, had some things of note. (Dates are approximate, and certainly don't reflect taping order.)