Nonprofit Gala Fundraising Games: A Complete Guide to Raffles, Wine Pulls, Squares, and More

How to Think About Fundraising Games

Before diving into specific formats, a few principles worth establishing.

Games are supplementary, not primary revenue

Even well executed fundraising games rarely generate more than $2,000 to $5,000 at a mid size gala. That is meaningful supplementary revenue, but it should never be positioned in the program where it competes with or displaces the paddle raise. The paddle raise, when properly designed and seeded, almost always represents the highest net revenue per stage minute of any element in the program.

Placement matters as much as the game itself

The best place for most fundraising games is the cocktail hour, before guests are seated and before the formal program begins. This is when energy is highest, guests are circulating, and there is no competition with the main event. Games that run during dinner risk losing the room's attention at a moment you need it. Games that run after the live auction risk deflating momentum you spent the evening building.

One or two games, not five

More is not more. A program that includes a raffle, a wine pull, a heads or tails game, a dessert dash, and a 50/50 is a program that feels chaotic and exhausting. Choose one or two formats that fit your audience and run them cleanly. The best revenue enhancers feel effortless. They generate money without making guests feel like they are being relentlessly solicited.

The goal of a fundraising game is not just to raise money. It is to raise energy. A game that gets people laughing, standing, and talking generates goodwill that translates directly into a more generous room when the paddle raise begins.

The Legal Landscape: What to Know Before You Run a Raffle

Raffles, 50/50 draws, and games of chance are regulated as charitable gaming under state law, and the rules vary dramatically from state to state. Before running any raffle at your event, your organization needs to verify compliance in its state.

Three states prohibit paid entry raffles entirely

As of mid 2026, Alabama, Hawaii, and Utah prohibit paid entry nonprofit raffles outright. Organizations in these states can run no purchase necessary sweepstakes instead, which removes the consideration element and sidesteps the gambling definition, though sweepstakes carry their own disclosure requirements.

Most states require a permit

The majority of states that allow nonprofit raffles require the organization to obtain a charitable gaming permit or license before selling tickets. Permit fees typically range from $15 to $500 depending on the state and the scope of the event. Some states limit raffle eligibility to 501(c)(3) organizations with a minimum period of existence, often one to five years.

Ticket design requirements

Many states have mandatory disclosure requirements for raffle tickets, such as the drawing date, time, and location, prize description, the organization's name and contact information, and permit number where applicable. Tickets that do not meet these requirements can create legal exposure regardless of whether a permit was obtained.

IRS reporting thresholds

For raffles conducted after December 31, 2025, federal reporting requirements changed under the One Big Beautiful Act. Nonprofits must file Form W-2G with the IRS, and provide a copy to the winner, when raffle prizes reach $2,000 or more, net of the wager, and at least 300 times the cost of the ticket. Winners are responsible for reporting prizes as income on their federal tax returns.

Online raffle ticket sales

Whether a nonprofit can sell raffle tickets online is the single most misunderstood question in raffle compliance. Rules vary widely by state. Some explicitly allow it, some explicitly prohibit it, and many simply never addressed it. California prohibits online raffle sales. New York allows them with prior approval. Texas, Ohio, and North Carolina have statutes that predate online fundraising and do not clearly address the question. When in doubt, limit ticket sales to your event venue and consult a qualified attorney in your state.

This guide provides general educational information only. Raffle laws change frequently and vary significantly by state. Always consult your state's charitable gaming office and a qualified attorney before selling raffle tickets.

Fundraising Games: A Quick Reference

Revenue ranges are illustrative based on typical mid size nonprofit gala audiences, 150 to 400 guests. Actual results vary significantly by audience, ticket pricing, and execution.

Game Deep Dives

The 50/50 Raffle

The 50/50 is the most universally understood fundraising game. Sell as many tickets as possible, draw one winner, and split the pot evenly, half to the winner and half to your organization. Its power is simplicity. Donors understand it immediately, the math is transparent, and the growing jackpot becomes a visible motivator as ticket sales accumulate.

How it works

Volunteers sell tickets during cocktail hour and dinner. Ticket price typically ranges from $5 to $25 each, with bundle pricing to encourage volume, such as five tickets for $20. Drawing happens during the program, ideally at a moment that creates energy, such as just before the live auction or during a program break.

Typical revenue

$500 to $3,000 at a mid size gala, depending on ticket pricing, volume, and how aggressively volunteers sell.

Best practices

Bundle pricing dramatically increases average purchase. Have volunteers circulate continuously rather than stationing at a table. Announce the running total periodically. A growing jackpot number motivates late purchasers.

Watch out for

State permit requirements apply in most states. Keep meticulous ticket records. If the winner's share could trigger IRS reporting thresholds, be prepared to collect winner information for Form W-2G.

The Wine Pull

A wine pull is equal parts fundraiser and party game. Wrap a collection of wine bottles so labels are concealed, ideally including a few premium bottles worth significantly more than the ticket price, and let guests pay to select a bottle at random. The mystery of what they might get drives participation, and the tangible take home prize makes it feel less like a donation.

How it works

Collect donated wine bottles of varying quality. Wrap each bottle identically so the label is completely hidden. Guests pay $20 to $30 per pull and take home whichever bottle they select. The mix should include mostly mid range wines, $15 to $30 value, and a handful of premium bottles, $75 to $150 value, to create the excitement of a potential big win.

Typical revenue

$500 to $2,500, depending on bottle count and ticket price. A pull with 100 bottles at $25 each generates $2,500 gross with zero prize cost if all bottles are donated.

Best practices

Keep the mix heavily weighted toward accessible wines, with three to five premium bottles scattered in. Announce that premium bottles are in the mix but do not reveal how many. The mystery is the point. Run during cocktail hour when guests are standing and in a browsing mindset.

Watch out for

Alcohol laws vary by state and venue. Some states require that wine used as prizes be specifically permitted. Some venues have liquor license restrictions on how alcohol is distributed.

The Reverse Raffle

The reverse raffle is the most sophisticated, and highest revenue potential, game format on this list. Unlike a traditional raffle where the first ticket drawn wins, in a reverse raffle the last ticket remaining wins the grand prize. Every drawing eliminates participants until one ticket holder is left.

The format builds extraordinary tension over the course of an evening because participants know exactly where they stand, either they are still in or they are out. As the field narrows, the remaining ticket holders become the center of attention in the room, which creates a shared experience that a traditional raffle cannot replicate.

How it works

Sell a limited number of high priced tickets, typically $100 to $500 each, with a total cap of 100 to 300 tickets. The grand prize is high value, such as a luxury travel experience, a significant cash prize, or a major item. During the event, tickets are drawn at intervals throughout the evening. Each drawing eliminates one participant. The final ticket holder wins.

Typical revenue

$5,000 to $50,000 or more, depending on ticket price, number sold, and prize value. The Chattahoochee Tech Foundation raised $56,125 at a single reverse raffle event. Organizations that include tiered prizes for the final five or ten remaining participants can increase participation and justify higher ticket prices.

Best practices

The reverse raffle works best as an entire event structure rather than a single element within a larger gala program. Spacing the drawings over cocktail hour, dinner, and the live program keeps participants engaged for hours. Allowing buy backs at a premium price, letting eliminated participants re-enter mid game, can significantly increase total revenue. Offering the final five participants a chance to split the prize adds a negotiation element that audiences love.

Watch out for

This format requires meticulous ticket management, a charismatic emcee who can hold the room across multiple drawing segments, and clear communication of rules before the event begins. State charitable gaming permits are required in most states. Do not attempt this format without experienced event management support.

The Golden Ticket Raffle

The golden ticket raffle is a premium variation on the traditional raffle. Sell a strictly limited number of high priced tickets, typically $100 each with a cap of 100 tickets, for a single luxury prize. The exclusivity of limited ticket availability and the quality of the prize create a different dynamic from a standard raffle.

How it works

Set a ticket limit, often 100 tickets at $100 each, for $10,000 gross. The prize should be premium and visually compelling, such as a luxury travel experience, a private chef dinner, or exclusive event access. Draw one winner during the event at a high energy moment. Some organizations allow the same consignment prize to be resold to a second winner, doubling the revenue on a single item.

Typical revenue

$10,000 to $40,000, with the upper range achieved when premium consignment prizes are resold multiple times. One organization raised $12,550 with a single Tuscan travel package as the prize.

Best practices

The prize selection is everything. A luxury consignment travel experience works particularly well because it has strong visual and emotional appeal, a clear aspirational value, and can be sourced at no upfront cost through a consignment provider. Market the raffle aggressively before the event. Pre event ticket sales are often more effective than event night impulse purchases at this price point.

Watch out for

State permit requirements apply. If ticket sales are to occur before the event, verify whether pre event and online sales are permitted in your state.

Heads or Tails

Heads or tails is one of the most effective pre auction room energizers in the benefit gala playbook. It gets every participating guest physically standing, creates immediate competitive engagement, and generates revenue in the $1,000 to $3,000 range with minimal overhead. Executed well by an experienced auctioneer or emcee, it transitions the room from dinner mode to fundraising mode in a way that almost nothing else can.

How it works

During cocktail hour, guests purchase an entry token, wristband, or paddle for $20 to $25. When the game begins, the emcee asks all participants to stand and make their choice, hands on head for heads and hands on hips for tails. The emcee flips a coin. Those who guessed correctly remain standing, and everyone else sits. Rounds continue until one person is left standing, who wins a prize, typically a donated item, a gift card package, or a bottle of premium wine or spirits.

Typical revenue

$1,000 to $3,000 at typical entry prices. Revenue can be significantly increased by allowing eliminated participants to buy back in at two to four times the original entry price at a strategic midpoint in the game.

Best practices

Run this game immediately before the live auction as the last element of the pre program. It gets guests out of their seats, creates laughter and table competition, and delivers the room to the auctioneer already energized. Offer one last chance to purchase an entry just before the game begins. Build in the option to buy back in. At a previous event, a $1,000 buy back surge was generated at the midpoint of a single game.

Watch out for

The legal classification of heads or tails varies by state. Some states treat it as a raffle requiring a permit, while others classify it differently. Verify with your state's charitable gaming office before charging for entry. Keep the game to ten or fifteen minutes maximum. It should energize the room, not exhaust it.

The Dessert Dash

The dessert dash is a gala specific game built around a simple, delicious premise. Tables bid for the right to be first to the dessert table. What it actually accomplishes is generating competitive revenue from table captains and corporate sponsors who have something to prove in front of their tablemates.

How it works

Before dessert service, the auctioneer or emcee announces that desserts are available, but only to tables that purchase the right to dash. Tables bid progressively for priority dessert access. The highest bidding table goes first, the second highest goes second, and so on. Tables pass a hat, envelope, or designated container to collect contributions from individual guests, then announce their collective total.

Typical revenue

$1,000 to $5,000 depending on table count and competitive dynamics. Corporate sponsored tables with competitive relationships tend to drive the game higher.

Best practices

This game works best when tables include corporate sponsors or board members who are motivated by friendly competition. The auctioneer's role is to narrate the competition and celebrate each table's contribution, making every participant feel like a hero regardless of the amount. Pair the desserts with a visual display. Beautifully presented specialty desserts create genuine desire to get there first.

Watch out for

The dessert dash can run long if not managed tightly. Build a firm time limit into the format. It also works less well for galas where tables are made up of strangers, since the competitive dynamic that makes it fun requires table level relationships.

$1 to $100 Squares: The Paddle Raise Warm Up

This is one of the most strategically underrated revenue enhancers in the benefit gala toolkit, and one of the most legally straightforward, because it is not a raffle or a game of chance at all. It is a pure donation activity with a visual completion goal.

A grid of 100 squares is displayed during cocktail hour or the silent auction period. Each square is labeled with a dollar amount from $1 to $100. Guests claim a square by donating that amount. There is no prize, no drawing, and no random element. When every square is claimed, the board is complete and the organization has raised more than $5,000.

How it works

Display a 100 square grid prominently in a high traffic area. Squares are priced at face value. The $1 square costs $1, the $50 square costs $50, and the $100 square costs $100. Guests claim squares by making the corresponding donation to a volunteer staffing the board. As squares are claimed, they are visually marked off, and the completion of the board becomes a visible goal that motivates participation.

Typical revenue

$5,050 when fully claimed, the sum of $1 through $100. In a well attended cocktail hour, a fully claimed board is an achievable goal with active volunteer staffing.

Strategic purpose

This game serves a function that most revenue enhancers do not. It invites guests who would not raise a paddle at the $100 fund a need floor to make a meaningful gift at whatever level they are comfortable with. A guest who donates $10 on the squares board has already given, and has already said yes to giving, before the paddle raise begins. That psychological priming has real value for the room's overall generosity.

Best practices

Staff the board actively. A volunteer who engages guests directly will fill a board that sits unattended will not. Frame the completion goal from the stage, such as, we have 23 squares left, anyone who has not yet claimed one, please find a volunteer before we sit down. Celebrate completion from the stage if it happens during the event. Keep the ask simple. Any amount from $1 to $100, find the square that feels right to you.

Why no permit is needed

Because there is no prize and no element of chance, every participant simply pays the face value of their chosen square and receives nothing in return beyond the satisfaction of contributing, this activity is a straightforward charitable donation, not a raffle or lottery under any state's charitable gaming law. This makes it one of the most accessible formats for organizations in states with strict raffle regulations, including Alabama, Hawaii, and Utah.

Basket Raffles

Basket raffles are a staple of school and community nonprofit events. Curated gift baskets are displayed during the cocktail hour and silent auction period, and guests purchase raffle tickets to enter a drawing for the basket of their choice. Unlike a traditional raffle where all tickets compete for one prize, guests direct their tickets to specific baskets they want to win.

How it works

Procure curated gift baskets from donors, sponsors, or internal committees. Themes work well, such as spa and wellness, date night, outdoor adventure, gourmet food and wine, children's activities, and sports memorabilia. Display baskets prominently during the cocktail hour. Guests purchase tickets, typically $5 to $20 each or in bundles, and deposit them into the container in front of the basket they want to win. Drawings are announced from the stage.

Typical revenue

$500 to $3,000 depending on basket count, quality, and ticket pricing. Well themed baskets with high perceived value drive the most ticket volume.

Best practices

Basket quality matters more than quantity. Four beautifully curated, professionally displayed baskets outperform twelve hastily assembled ones. Baskets with clear aspirational themes, such as a wine country weekend, a year of golf lessons, or a spa day for two, generate significantly more ticket purchases than generic assortments. Post the estimated basket value visibly to anchor perceived worth.

Watch out for

Basket raffles require charitable gaming permits in most states. Because each basket has a separate ticket pool, record keeping across multiple baskets requires more administrative attention than a single prize raffle.

Sequencing Games Within Your Program

A Note on Games and the Paddle Raise

The single most important thing to understand about fundraising games is that none of them should compete with the paddle raise. The fund a need appeal, when properly seeded, structured, and called by an experienced auctioneer, is the highest net revenue per stage minute of any element in your program.

Games that run long, games that exhaust your volunteers, and games that create a sense of relentless solicitation all subtract from the generosity reservoir your guests bring to the paddle raise. The best revenue enhancers leave guests feeling energized and entertained, not solicited.

If your paddle raise has plateaued and you are wondering whether more games will help, the answer is almost always no. The paddle raise plateau is almost always a structure and seeding problem, not a supplementary revenue problem. More cocktail hour games do not fix a poorly designed fund a need ladder.

Key Takeaways

• Games and revenue enhancers are supplementary to, not replacements for, a well designed live auction and paddle raise. Choose one or two formats and execute them cleanly.
• Cocktail hour is the best placement for most games. Guest energy is high, the browsing mindset is active, and there is no competition with the main program.
• The highest revenue game formats, reverse raffles and golden ticket raffles, can generate $10,000 to $50,000 or more but require more planning, permit compliance, and experienced event management.
• Low overhead formats, such as 50/50, wine pull, heads or tails, and $1 to $100 squares, are accessible for most organizations and can generate meaningful supplementary revenue with minimal preparation.
• The $1 to $100 squares board is the only game on this list that requires no charitable gaming permit in any state, because it is a pure donation activity with no prize and no element of chance. It is also one of the most strategically useful. It primes guests below the paddle raise floor to say yes to giving before the fund a need begins.
• Raffle compliance is non negotiable. Verify your state's charitable gaming requirements before selling a single ticket. Alabama, Hawaii, and Utah prohibit paid entry raffles outright. Most other states require a permit.
• If your paddle raise has plateaued, the answer is almost never more games. It is better seeding, a better ladder structure, and better execution of the fund a need itself.

Ready to See What Your Data Reveals?

If your galas have plateaued and you're not sure whether the issue is your program pacing, your paddle raise structure, or your revenue mix, our Event Fundraising Consultation is available nationwide for $500. We analyze multiple years of your event data through our proprietary analytics engine and deliver a written recommendations report and a one-hour strategic presentation, no travel required.

For organizations in the greater Washington, DC metropolitan area, Capital Benefit Auctions also offers full-service live auctioneering and pre-event strategy, including game selection, run-of-show integration, and event-night execution.