$5,495,245.00

  1. Ready to start winning?
    Fill out the form to purchase our 3 Month Newsletter Subscription and a chance to play and win thousands of dollars every week!

  2. Please type your full name.
    Invalid email address.
  3. Invalid Input
    Invalid Input
  4. Invalid Input
    Invalid Input
  5. Invalid Input
    Invalid Input
  6. Choose a Subscription Length



    Invalid Input
  7. Invalid Input

  • Print Your Puzzle

    Print your entry puzzle at home.

  • Complete It!

    Enjoy & complete your puzzle at home. Fill in the entry form and include your entry fee.

  • Mail Your Puzzle

    Send your puzzle back to us. Include your entry fee & completed entry form.

  • Win Cash Prizes!

    Accurately complete the puzzle to win cash prizes.
  • 1

  • 6 Month
    Challenging Times Subscription
    $25

    Buy Now

  • 12 Month
    Challenging Times Subscription
    $40

    Buy Now
  • 1
  • Pam has won $21,389 so far!

    Pam has won $21,389 so far!

    My experience, throughout the years, is that Challenging Times has always been thoroughly honest and reliable, offering a good variety of fun puzzles every week. The reporting of puzzle solutions and the winners is always timely and on schedule, as is the distribution of the prizes. The rules for the puzzels are easy to follow. It is a very great pleasure to take part in the fun and honest games that Challenging Times offers.
  • Ed Dansereau, MA, has won $16,633

    Ed Dansereau, MA, has won $16,633

    "I want you to know how much I enjoy your word success puzzles, win or not. It sure keeps my mind alert."
  • Patricia Bradley, IL, has won $41,281

    Patricia Bradley, IL, has won $41,281

    "I enjoy the challenge and intrigue. I also find it very helpful in obtaining a better vocabulary."
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11