ADVERTISEMENT

December 2025 Featured Winners

‘Tis the season to win cash prizes with Winstakes! What a wonderful time of year to come into some extra spending money to add to your holiday fun! It’s always free to enter every day, and when you win you’ll get an email to collect your cash prize free of charge too!

Denise R. from Waldorf, Maryland, starts us off with the first $50 Weekly Cash Prize win of the month on December 1, which is definitely a great way to begin the holiday season! You might decide to meet a friend at Momi’s Kitchen to enjoy a relaxing lunch together before the hustle and bustle of holiday preparations start to kick in. They’ve got an impressive menu filled with tasty homestyle choices along with excellent service and soft music to round out your leisurely meal.

Dirk S. in Duquesne, Pennsylvania, won the $25 Daily Cash Giveaway on December 3, and chose to receive it as an Amazon gift card, which is always a fun place to shop online no matter what you’re in the market to buy. That’s one of three ways our winners can collect their prize money. PayPal and a check by mail are the other options. For larger cash prizes we will send a check, but who can argue with a big free check with their name printed on it?!

Alonso A. of Converse, Texas, won the $50 Weekly Cash Prize drawing on December 9, and could be heading over to The Hayden to meet up with friends for sandwiches and cocktails in this hip eatery that offers a cool retro vibe with great menu choices and amazing drinks. They also host a fun happy hour, so there’s another option of how you can enjoy yourself!

Steve M. from Toronto, Ontario, Canada, won the $25 Daily Cash Giveaway on December 13, and requested PayPal to receive it. When that hits his bank account it converts to about $34.70, so there’s a nice chunk of change to perhaps meet your friends at Ruby Soho for happy hour after work. They have amazing deals on food and drink from 5 – 7 pm every weeknight, so that could be a great reason to get together and toast the holiday season with each other.

Robert M. in Brookhaven, Mississippi, won the $75 Cash Sweepstakes on December 18, which is just in the nick of time for last minute holiday preparations. You might head over to The Great Mississippi Tea Company to pick up some gift baskets for the tea lovers on your list. There’s no better place to buy tea, and a visit to the farm is a delightful experience as well. You might decide to bring your significant other and take the tour, sip some of their fine tea and visit the gift shop while you’re there. It sure is amazing what these folks do to keep this farm award winning!

Richard K. of Jonesboro, Arkansas, won the $50 Weekly Cash Prize drawing on Christmas Day, December 25! That’s like getting an unexpected gift and we hope it made your holiday even more merry and bright! You might plan to take your spouse out for a nice lunch at Skinny J’s to enjoy a nice meal together and continue your holiday celebrations!

Bonnie G. of Palm Harbor, Florida, has some extra cash to use as she pleases since winning the $100 Cash Sweepstakes on December 28! That could be perfect to go out to dinner with your special someone on New Year's Eve and get home in time to watch the ball drop in Times Square. The Lucky Dill could be the perfect spot since it’s a New York themed restaurant featuring deli style casual dining inspired by the Big Apple.

Harry S. in Addison, Texas, won the last $25 Daily Cash Giveaway of the month and the year on December 31, which sure is a nice way to head into 2026 with some extra money in your pocket! You may decide to meet up with your buddies at Holy Burger to enjoy a fresh hamburger with all your favorite fixings. It may be considered fast food, but they take meticulous care to prepare each order and make sure their customers are completely satisfied! Everyone says it’s well worth the wait, the service is impeccable and the food never disappoints.

Stay tuned for more winner news and keep entering daily, we’d love for you to win too!