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

    Buy Now
  • 12 Month
    Challenging Times Subscription

    Buy Now
  • 1
  • Patty P. has won $17,781 so far!

    Patty P. has won $17,781 so far!

    Patience, perseverance, persistence - all are needed to successfully complete these puzzles. Implementing these strategies has made me mentally, intellectually, emotionally and financially richer and sharper.
  • Suzanne Borash, MN, has won $46,945

    Suzanne Borash, MN, has won $46,945

    "I have always loved doing word puzzles and learning about different topics. Challenging Times offers the opportunity to do both. I particularly enjoy Winning Words because it’s fun researching the answers and unscrambling the letters. The Presidents Payoff, States, and State Capitals puzzles help sharpen memory…. Thank you, Challenging Times, for making life more fun!"
  • Robert Arthur, AZ, has won $81,673

    Robert Arthur, AZ, has won $81,673

    "Years ago I almost didn’t send $5.00 to play Challenging Times puzzles. Boy! Am I glad I did! Now weekly (for years), I can hardly wait for the Challenging Times to arrive. Eagerly I open the envelope to see how many puzzles I’ve won and how much prize money….Working puzzles and “winning” money is fun."
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11