$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
  • Marilyn Baker, OH, has won $70,647

    Marilyn Baker, OH, has won $70,647

    "Thanks to the Challenging Times I have an interest that I can pursue. It not only keeps my mind occupied, but also challenged." 
  • Bill Baranowski, NV, has won $7,914

    Bill Baranowski, NV, has won $7,914

    "My love of words has helped me to win several times."
  • Dan has won $25,340 so far!

    Dan has won $25,340 so far!

    Challenging Times has been an exceptional puzzle club that I have been amazed with over the last 13 years. If anyone is willing to challenge their mind with puzzles and earn supplemental income then Challenging Times is the way to go!
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11