Win $1,000 + a Year of Free OLIPOP in the OLI-Day Cheer Sweepstakes

What if your soda obsession could actually pay you back? The OLIPOP Holiday Cheer Sweepstakes (also called the “OLI-Day Cheer Challenge”) is handing out serious prizes this holiday season—think a $1,000 Visa gift card and a year’s worth of OLIPOP delivered straight to your door. Yep, this isn’t your typical “win a free can” moment. This nationwide sweepstakes runs through December 31, 2025, and it’s designed to reward both loyal OLIPOP drinkers and free-entry fans alike.

Here’s what makes this promotion especially fun: it combines OLIPOP’s holiday loyalty campaign with weekly prizes, a huge grand prize, and even an alternate free entry option (no purchase needed). You can enter once per day, and every valid entry gets you into the drawing for that week’s prize—and the big one at the end. With eight separate weekly drawings, plus a final grand prize pull, there are plenty of chances to win.

If you love giveaways that mix free entries with lifestyle rewards and cash, this one is worth your time. Below, we’ll break down everything—how to enter, what you can win, and how to make sure your submission actually counts.

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PRIZE BREAKDOWN

Let’s talk about the part everyone actually cares about: the prizes. OLIPOP isn’t holding back.

Grand Prize (1 Winner):

• A 12-month supply of OLIPOP—two cases per month for a full year (that’s 24 cases total, valued at about $34.99 each).
• A $1,000 gift card to spend however you want, whether that’s on groceries, travel, or more soda.
• An OLIPOP Yeti beanie (because apparently, the Yeti mascot is a whole vibe this year).
  Total value: $1,854.01

Weekly Prizes (8 Winners, one per week):

• A three-month supply of OLIPOP—two cases per month for three months.
• One OLIPOP Yeti beanie.
• A $100 gift card.
  Each weekly prize package value: $324.19

In total, the sweepstakes is giving away over $4,447 in prizes, combining free products, branded merch, and spendable cash.

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WHAT YOU CAN DO WITH THE PRIZE IF YOU WIN

Let’s be honest—winning $1,000 plus a fridge full of OLIPOP opens up endless possibilities. First off, you can finally stock up on every one of their trendy, low-sugar flavors—Vintage Cola, Strawberry Vanilla, and Ginger Ale are cult favorites for a reason. With two cases arriving monthly, you could have a permanent “soda bar” at home, or keep them chilled for guests through New Year’s, birthdays, and every random Tuesday.

That $1,000 Visa gift card? It’s digital, so it’s as flexible as cash. Use it toward your next grocery haul, fund a little holiday shopping spree, or even offset bills—whatever feels right. The best part is that this isn’t a brand credit; it’s spendable anywhere Visa is accepted.

And the Yeti beanie? It’s not just for laughs. OLIPOP’s winter merch drops tend to sell out fast, so you’ll have something exclusive and Instagram-worthy. Whether you’re cozying up for movie nights or hitting the slopes, that Yeti branding makes it the perfect low-key flex.

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Q&A

Is this legitimate?
Yes—completely. This sweepstakes is sponsored by OLIPOP, Inc., headquartered in Oakland, California. It’s a verified, publicly hosted sweepstakes, and all details are published in their official rules on the OLIPOP website.

How many entries are allowed?
You can enter once per day during the entire Sweepstakes Period. That means up to one daily entry between November 5 and December 31, 2025.

Are there bonus entries?
No bonus entries are listed—each person is allowed one entry per day, regardless of entry method.

Is it a one-time entry or daily?
This is a daily entry sweepstakes, meaning you can return every 24 hours to submit another entry and increase your odds.

How can I enter for free?
You can skip the purchase completely. Use the free online entry form (AMOE) here: https://drinkolipop.com/pages/ocs-amoe. Just fill in your name and email address—no receipt or product required.

How many prizes can one person win?
Each person can win only one prize package—so if you win a weekly prize, you won’t be eligible for the grand prize.

When do entries close?
All entries must be submitted by December 31, 2025, at 11:59 PM PT.