PrizeCastle Winners Roster May 2026
Welcome to PrizeCastle, the kingdom of opportunities to win cash and prizes completely free! Each month, we feature those fortunate winners to congratulate them and inspire others who may be wondering if they can win as well.
If you’re not sure you can win when entering PrizeCastle, just ask Pete A. of Coldwater, Ohio. That is, when he returns from the $10,000 Disney Family Trip he won on May 21! Talk about a magical adventure! This is indeed the place where fairy tale dreams can come true! There’s a very good reason they call it “the most magical place on earth!” You and your family will enjoy an immersive experience filled with characters that come to life, a magical castle to explore, entertainment and attractions, tours and special events, and enchanting extra experiences that are sure to fill your family photo album with many fond memories.
You’ll also have over 400 dining options and find your “happily whatever you’re after,” with shops, restaurants, and special moments you can indulge in until your heart’s content! It’s certainly going to be a spectacular time filled with so many magical moments and smiles! Add to that, you’re just in time to explore the “cool kids of summer,” which offers limited-edition adventures, classic beloved attractions, shows and entertainment, and special offers at Hollywood Studios, EPCOT Center, and the Magic Kingdom park. It’s certain to be the time of your lives. Congratulations, Pete! We are completely thrilled to award this phenomenal prize to you and hope you and your loved ones have the best time you’ve ever had in your lives!
Tray W. of Gilmer, Texas, might be off on some adventures of his own with his new trusty sidekick, the Apple Watch SE he won on May 20! This smartwatch offers health and safety features such as heart rate monitoring, fall detection, and fitness progress tracking, and can pair seamlessly with your iPhone, giving you all the benefits of having this amazing smart device on your wrist. You’ll certainly be the envy of everyone in your castle when they see you flick your wrist or double-tap the screen, which is made with crack-resistant glass for safety and longevity. You’ll certainly be fashionable when you wear it too, and can change the face to suit your own personal style. This is certainly a modern watch which is built to last and will be something you can rely on throughout your busy days!
Mary E. from Evansville, Indiana, might be gearing up to host a tournament at her house since winning the Medieval Chess Set & Board on May 6! This is certainly a great accessory to complement your home décor, and a great addition to family fun or game nights with friends. The pieces are like works of art to be admired, or like an army to fight a battle until you emerge “checkmate” victorious! Whether you’re an avid chess player or just learning, this is the type of set you will pass down through the generations, with all the family stories that are sure to be something to treasure!
Carlos S. of Albert Lea, Minnesota, is a frequent sweepstakes winner who knows that maximizing all of your free daily entries gives you the most chances to win, whether it’s something big or small. On May 1, he won the $5 Daily Cash Prize drawing to add to his tally of lucky wins! While, of course, it’s just $5, it’s five dollars more than you had before, which you can tuck in your wallet to save as extra money for anything at all!
Lasonia M. in Goldsboro, North Carolina, is also an avid player who wins quite often, and this month she won the $5 Daily Cash Prize drawing on May 9. That might be just what you need to enjoy lunch at McDonald’s. Their menu offers some tasty choices, like a $5 Value Meal that comes complete with a double cheeseburger or fish fillet sandwich, soda, fries, and chicken nuggets with dipping sauce. Now, five dollars doesn’t seem so small after all, does it?!
Anne L. of Owen Sound, Ontario, Canada, also knows that entering every sweepstakes every day is the best way not to miss a single chance to win, and on May 27, she too won the $5 Daily Cash Prize drawing, which actually converts to more than $7 in Canadian dollars. That could go towards a tasty stack of breakfast pancakes at Stacked Pancake Breakfast House, with a nice hot cup of delicious coffee to enjoy with it!
Congratulations to all the PrizeCastle winners in May! Be sure to visit the site, cross the drawbridge, and submit your free entries every day for the chance to win prizes including cash up to $888,888.88 and fun prizes that can make your visit an exceptional day in the castle!