We serve a wide variety of groups on Cheddar Up—from schools to HOAs to churches to small businesses to friends—and their collection needs are even more diverse. But we seem to have found common ground across them all: a March Madness fundraiser. The adage must be true: sports unite everyone.
Take a look at some of our favorite bracket competitions.
***Be smart about your fundraising! Note that raffles may be subject to specific regulations or prohibited in certain states. It is the sole responsibility of users and participants to ensure compliance with their local laws. For more information on conducting raffles, bingo, auctions, and other games of chance as a charitable nonprofit, click here.***
1. Office buy-in with the option to buy 1, 2, or 3 brackets
The competition in office bracket pools can get intense!* Many of our Cheddar Up collectors choose to offer multiple bracket options—letting participants buy 1, 2, or 3 entries for added flexibility.
To keep things organized, use customizable receipts to send the link to your online bracket pool automatically. For a seamless experience, set your collection to close before game time, preventing late entries and keeping everything fair.
How it works: Participants submit an entry fee for the number of brackets they would like to purchase, and then they will be sent a link to the online bracket platform you’ve chosen. Once the tournament starts, the points assigned to each correct pick determine the winners. You can set the rules—winner takes all, top three prizes, or a mix of cash and donated giveaways.
*Intense means we’ve seen office pools exceed $4,500! That’s a lucky winner.
2. Community March Madness fundraiser with prizes for top 3 winners
Want to engage a bigger crowd? Schools, PTAs, and nonprofits have used this community bracket template to run public fundraisers where participants donate to enter. Some groups even secure local business sponsorships to match donations, doubling the impact!
How it works: Set a fixed donation amount for entry, customize the template with your details, and share the link with your community. Throughout the tournament, you can update participants with standings and results via Cheddar Up’s built-in messaging tools.
3. March Madness fundraiser that splits the winnings
A March Madness bracket fundraiser is a simple and exciting way to raise money for athletic programs, school clubs, booster groups, and more. A popular approach? Split the winnings—half goes to your organization, and the other half goes to the winner. This setup incentivizes participation while ensuring a successful fundraiser.
How it works: Use this fundraiser template to collect buy-ins for bracket entries. Set a fixed entry fee, then track brackets as the tournament unfolds. In the end, award half the pot to the highest-scoring bracket and keep the other half for your group’s fundraising goals—whether it’s new team uniforms, travel expenses, club activities, or school improvements.
4. School or alumni “squares” March Madness fundraiser
For a simple and engaging alternative to brackets, many groups—including alumni associations and school fundraisers—have turned to March Madness Squares as a fun and flexible way to raise money. While squares games are often associated with football, they work just as well for basketball and are popular for March Madness fundraisers.
How it works: Start with a 10×10 grid of 100 squares and sell each square for a set price (for example, $10 or $50 per square). Once all squares are purchased, numbers 0-9 are randomly assigned across the top (winning team) and down the side (losing team).
At the end of a game, the last digit of each team’s final score determines the winning square. For example, if the final score is 85-81, you’d find “5” on the top row and “1” on the side column. The person whose name is in the winning square takes home the prize—whether it’s cash, a gift card, or school spirit swag.
This low-maintenance game keeps people engaged throughout the tournament while bringing in funds for your cause. Many groups even choose to have multiple winners—payouts at halftime, at the end of regulation, or for different tournament rounds—making it even more exciting!
*The average earnings for sports squares is around $2500, but depends on how much your squares cost. This example will earn $5000 if all 100 squares sell, plus more if they do multiple grids. Your net will depend on what you decide to pay out.
5. School PTA March Madness fundraiser with daily raffles
A March Madness raffle is a great way to add excitement while raising funds for a cause. Schools, PTAs, and nonprofits have used this approach to raffle off everything from sports memorabilia and event tickets to local business gift cards and school fundraisers. Some groups even turn it into a multi-day event, drawing winners throughout the tournament to keep engagement high.
How it works: Sell online raffle tickets through Cheddar Up at a set price—for example, $10 per entry or bundle deals for multiple tickets. You can hold a single grand prize drawing at the end of the tournament or choose daily or weekly winners to build momentum.
Want to boost participation? Add a fundraising progress bar to show how close you are to your goal, or include an attachment or link so donors can see exactly what their contributions are supporting. With Cheddar Up’s report center, managing entries and drawing winners is simple—just set it up, share the link, and start raising funds!
6. Special school basketball game
March Madness isn’t just for the pros—schools have turned the excitement into their own fundraising events! One creative way to get students involved is by hosting a basketball game, like a students vs. teachers showdown or a grade-level tournament. These events unite the school community while raising money for a cause, like new sports equipment, field trips, or a school improvement project.
How it works: Sell game tickets in advance using this student game template—offering single tickets or discounted bundles for families. Use point-of-sale checkout at the door for last-minute ticket sales. Some schools even add extras like a half-time raffle, snack sales, or donation options to maximize fundraising.
In short, before you go
A March Madness fundraiser is an easy way to capitalize on a seasonal event to support your group. You can collect donations with a bracket pool or a related event, and Cheddar Up will manage the receipts and records.
