$25,000 Birthday Challenge Q99 $25,000 Birthday Challenge You could win $25,000 just for having a birthday!! Listen to Q99 to win 3 times every weekday: 8:40 AM, 11:40 AM and 3:40 PM. At each play time we announce a month of the year. If you were born in that month be the 19th caller and you’ll automatically win $100. Then, if your birth date matches our predetermined day of the month, you’ll get upgraded to $500. And, if your birth year matches our predetermined year, you’ll win $25,000!!! Get the official rules here