Monkey Island, get ready. The 4th Annual Cinco de Poker Derby is shaping up to be the biggest, wildest, most action-packed Derby yet. Grab your best poker face, hop on your golf cart — or rent one for the day — and join hundreds of your closest friends for a day of cards, laughs, live art, live auction action, and epic prizes. All for a great cause. And yes, you'll be watching the Kentucky Derby on the big screen at Big Shots when the race goes off at 5:45.
What to Expect
Poker Run Cash Prizes 💰
🏆 Winners
🥇 1st Place — $500 CASH
🥈 2nd Place — $300 CASH
🥉 3rd Place — $150 CASH
🃏 Receive 1 free card at each stop. Visit 5 official stops + 2 wildcard stops to build your hand.
💵 Buy up to 3 extra cards per stop for $5 each — the more you play, the better your odds.
Winners announced at Big Shots before the live auction — find out if you're walking away with cash first.
Derby Style Contests — Win $250!
We're bringing the Derby flair to Monkey Island this year with TWO chances to win big. Get creative, stand out, and let's see who takes it home.
👒 Best Derby Hat
Audience judged at Big Shots. Bring the bold, the classy, or the outrageous.
Prize: $250 Shebang's Gift Card
🚗 Best Decorated Golf Cart
Judged by a hand-picked panel. Turn your cart into a rolling party.
Prize: $250 Shebang's Gift Card
Winners announced at Big Shots on May 2, 2026.
Pre-Registration Events
Skip the long lines on Derby Day! Pre-register at one of three April stops. Each location will have food and drink specials, good vibes, and Derby details handled ahead of time. The raffle golf cart will be on-site at each stop too.
| Date | Location | Hours |
|---|---|---|
| Saturday, April 11 | The Quarterdeck at Tera Miranda | 12:00 PM – 5:00 PM |
| Saturday, April 18 | The Shebang | 4:00 PM – 8:00 PM |
| Saturday, April 25 | Market 216 | 11:00 AM – 2:00 PM |
Can't make a pre-registration event? You can also register online anytime. With close to 400 participants expected, pre-registering is strongly encouraged.
VIP Experience — Bidding Open Now
🚗 Cinco de Poker Derby VIP Experience
Want to experience Derby Day like a straight-up VIP — showing up, being taken care of, and enjoying every second? The winner is drawn before the event so you can roll in on May 2nd already set up.
- Private Golf Cart + Chauffeur — All Day
You and your crew (up to 5 people) get a dedicated driver from stop to stop. No parking headaches, no waiting, no stress. - Priority Access at Every Stop
Roll in like you own the place — from registration all the way to the final party at Big Shots. - VIP Table at Big Shots
Reserved front-row seating for the live auction, entertainment, and after-party — front and center. - Food + Drinks Covered
1 drink ticket per guest at Big Shots + entrée voucher for The Forge Food Truck per guest.
🎟️ Raffle — $25 Per Ticket
WIN A CUSTOM
GOLF CART 🛺
A fully custom-built 2021 EZGO TXT Gas by Golf Cart Guyz. Don't need to be present to win. Winner announced live after the auction.
Get Raffle Tickets — $25 Each →Golf Cart Specs & Details
One lucky winner drives away in this fully custom Golf Cart Guyz build. Raffle tickets are $25 each. You do not have to be present to win — the winner will be announced live on Facebook after the live auction on Derby Day.
Cart specs:
- 2021 EZGO TXT Gas
- New body & headlights
- 5" lift with MODZ struts & UV top
- 15" Spider wheels / 23" GTW Tires
- Premium white seats & Genesis 250 backseat kit
- 36" Bazooka light bar
- MadJax front bumper & nerf bar steps
- 5-panel toggle switch with USB charger
- Push button start & custom steering wheel
- Heavy rubber floor mat & rear view mirror
Built by Golf Cart Guyz — (918) 257-1749 | thegolfcartguyz.com
Get Raffle Tickets — $25 Each →Live Auction — 7:00 PM at Big Shots
The live auction kicks off at 7:00 PM at Big Shots on Monkey Island. Local restaurants and businesses have stepped up with serious donations, and every package is built around a full Grand Lake experience. Come ready to bid — these will go fast.
🏨 The Ultimate Grand Lake Experience
This is the premier package hitting the auction block at the Cinco de Poker Derby — a full luxury weekend on Monkey Island built for relaxation, golf, great food, and lake life done right.
- 2-Night Stay at Shangri-La Resort
- Access to the newly renovated resort pool
- Golf for Two at Shangri-La Golf Club and The Battlefield Course
- $200 Gift Card to South 125 Bar & Grill
- Weekend Golf Cart Rental courtesy of Golf Cart Guyz
📍 Live Auction — 7:00 PM · May 2, 2026 · Big Shots, Monkey Island. Bring your bidding game — this one moves fast.
🏄♂️ Surf & Swine Experience
Grab your crew, hit the water, and then roll straight into one of the best spots on the lake to eat, drink, and celebrate. This isn't just an item… it's a full-blown Grand Lake experience.
- 4-Hour Wakesurf Experience with Barefoot Wakes on Grand Lake — professional instruction, premium surf boat, unmatched lake day vibes
- $250 Gift Card to Blind Swine on Duck Creek — food, drinks, and post-surf celebration
🔥 Live Auction · 7:00 PM · May 2, 2026 · Big Shots, Monkey Island
🥩 Smoked BBQ Experience
A heavy hitter hitting the block — The Market at 216 has stepped up in a big way. This isn't just food… this is the centerpiece for your next lake weekend, party, or get-together. Feed a crowd and be the hero without lifting a finger.
- Freshly Smoked Brisket
- Smoked Pork Butt
- Cooked low & slow to perfection
- Feeds a crowd — perfect for any gathering
💥 Live Auction · 7:00 PM · May 2, 2026 · Big Shots, Monkey Island — this one will bring the heat.
🌅 Dinner on the Water + Private 2-Hour Sunset Cruise for 8
The ULTIMATE Grand Lake experience — start your evening with dinner at the marina with incredible waterfront views, then step aboard for a private 2-hour sunset cruise across Grand Lake. This is the kind of night people talk about all summer.
- Dinner for your group at the marina with waterfront views
- Private 2-hour sunset cruise on Grand Lake
- Up to 8 people — perfect for couples, friends, or clients
- Prime sunset views on the water, fully private experience
This package will go FAST. Come ready to bid.
💥 4 Water Chairs + Premium Lake Package
Locally owned and assembled right here on Grand Lake, Grand Floats has donated 4 Water Chairs — and these aren't your average pool floats. Built for all-day lake hangs, keeping your drink close and your crew comfortable whether you're at the sandbar or tied up with friends.
- 4 Grand Floats Water Chairs — locally made on Grand Lake
- Paired with other premium items for a complete Grand Lake experience package
- Float all day. Drink in hand. Zero stress.
🥂 Ultimate VIP Night Out Package
One of the biggest packages of the night — built for a group that's ready to go all-in. Start with a world-class dinner, roll out in style, and arrive like you own the place.
- $500 Gift Card to Speedy's Chophouse — start the night right with a classic steakhouse dinner
- 3 Hours on the Prime Time Charters Party Bus — lights, music, BYOB, and nonstop fun for your crew
- Big Shots VIP Experience (Up to 10 Guests)
- 2 top shelf bottles (plus set-ups)
- 18 domestic beers
- Champagne sparkler presentation
- Private VIP seating area
- Free VIP admission — skip the line
💥 Bring your friends. Pool your bids. WIN the night. This is THE group experience of Derby night.
Benefiting Two Great Causes
🏝️ WAAMI – Women's Auxiliary Association of Monkey Island
WAAMI is the 501(c)3 organization behind the Cinco de Poker Derby. They receive and distribute donations to different local charities around Grand Lake and Monkey Island, making a direct impact on the community.
❤️ Toby Keith Foundation – OK Kids Korral
The OK Kids Korral provides a cost-free, home-like environment for pediatric cancer patients and their families while receiving treatment in Oklahoma City.
Ready to Play?
Register online, grab raffle tickets, and mark your calendar for May 2nd. This is the biggest Cinco de Poker Derby yet — don't miss it.
Get Raffle Tickets — $25 Each →More About Monkey Island
The Cinco de Poker Derby takes place on Monkey Island — Grand Lake's premier entertainment peninsula. If you're making a weekend of it, check out our guides to Monkey Island, waterfront restaurants, and lodging options at Grand Lake.