January 2026 Featured Winners

The new year is off to an awesome start, with so many lucky winners to congratulate! There’s nothing better than getting an email from Winstakes saying you’ve won a cash prize! No matter how much you win, it’s always free to enter, win, and collect your prize money, which can be used for anything you choose!

Steven W. from Birmingham, Alabama, won the very first $25 Daily Prize of the month and year on January 1, which sure is a great way to start off with that good news. That might set the tone for more good luck and prosperity throughout the coming year! You never know what could happen next if you keep entering daily!

David C. in Vero Beach, Florida, put some money in his wallet after winning the $75 Cash Prize on January 5! Perhaps you’ll take your spouse out for a nice lunch at Seaside Grill to enjoy a beautiful view with a delicious meal and your favorite beverages. A table on the patio with a fresh ocean breeze is always a great accompaniment to a wonderful meal!

Benson E. of San Leandro, California, must be in a celebratory mood since finding out he won the $750 Cash Prize on January 8! That’s quite a nice chunk of money that can be enjoyed in so many different ways! This could be just what you needed if you were hoping to get tickets to see Van “the man” Morrison at the Palace of Fine Arts in San Francisco. He’s performing a limited engagement series of shows in February featuring his new blues-inspired material, and a very special guest, his daughter, Shana, will be on stage! It’s sure to be a night to remember!

Jerimah F. from Chiloquin, Oregon, is among our $50 Weekly Cash Prize winners, having won the prize drawing on January 10! We award this cash prize to one lucky winner every week, so be sure to submit your daily entries and watch your email inbox! That’s free money you can use to fill up your gas tank, buy some groceries, or perhaps you’ll take your special someone out for lunch at the Burger Shack for a perfectly cooked quarter-pounder with cheese, fried pickles, and a tasty shake! This is the place when it comes to the best burgers in town!

Ron S. in Mansfield, Ohio, is all set to have a fun time shopping online with the $250 Cash Prize he won on January 14, since he chose an Amazon gift card to receive his winnings. We offer our winners three choices to collect their free prize money. A check by mail or PayPal are the other two options, and all you have to do is reply to your winner email to tell us which way you want to receive it.

Betty B. of Suwanee, Georgia, won the $25 Daily Cash Prize on January 18, which could pay for your family’s favorite pizza from Two Cities Pizza Company, where you can choose between New York and Chicago styles and build your own with your favorite toppings, sauce, and size. If you’re watching your calories, you can also get a cauliflower crust topped with anything you like, including an assortment of veggies and your choice of a variety of types of cheese.

Stevie N. from Greenwood Springs, Mississippi, won the $100 Cash Prize on January 29, which is definitely an exciting email to receive! That could mean a fun night out at The Gemstone to meet up with your friends for drinks and a phenomenal dinner! Everything on their menu receives high marks, and the wait staff is equally impressive, making it the perfect place to celebrate! This is the place where everyone knows your name!

Samuel D. in Pittsford, New York, landed the last $25 Daily Cash Prize of the month on January 31, which sure is a nice surprise because winning any amount of free money is enough to put a smile on your face! You may decide to treat yourself to lunch at Hungry’s Grill, where you can get a perfectly cooked-to-order burger with crunchy homestyle fries and homemade macaroni salad for less than twenty dollars, so you can also leave a nice tip!

Congratulations to all the lucky winners this month! Keep entering daily to win again, or win for the first time, because one thing is for sure, we’d love for you to win! It’s always free and easy to submit your daily entries using the best email address where you can be reached, so you’ll find out right away when you win!