This is for getting a 5 win streak in daily challenges.
On the main menu, where you see New Game, Challenges, etc., press Tab to go to the daily challenge page. A new run appears every day at 4am Central Time.
While you do have to reach the end and win 5 times, it's not 5 DAYS in a row, just 5 attempts. Say you win on monday and tuesday, but can't play on wednesday as you are too busy. As long as you win the next time you play, the win streak continues.
But you should try to play every day, as playing 31 days in a row will get you