The Cougar Classic Trivia Night & Auction is Overland Trail Elementary PTO’s largest fundraiser of the year — and our most fun adults-only night out!
At its core, The Cougar Classic is a community par-tee with a competitive twist — an adults-only night out filled with friendly rivalry, big laughs, and one team earning championship bragging rights.
Join us for:
- 🧠 10 rounds of high-energy trivia
- 🎧 A live DJ
- 🛍️ Silent Auction
- 🎤 Live Auction
- 🎉 A few surprises throughout the night
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Registration Options
You may register for a Team Table, Teacher Table, or as an Individual.
🏆 Team Tables
- 12 Team Tables available
- Up to 10 people per table
- $400 per table
One Team Captain registers the table. Team members can settle up with the Captain offline.
If you know your team members at registration, please include their names and email addresses for event communication.
🍎 Faculty Team Tables
- 3 Faculty Tables available
- Up to 10 faculty members per table
- Must be comprised of 50% or more faculty members
- $200 per table
We LOVE seeing our teachers in the mix!
🤝 Individual Registration
- $40 per person
Register solo and we’ll seat you at one of our Community Tables and build teams from there.
No team? No problem.
How Trivia Works
There will be:
- 10 rounds
- 10 questions per round
- A wide array of categories
- A mix of multiple choice, true/false, and open-ended questions
An emcee will read questions aloud, teams submit answers each round, and the team with the highest score at the end wins bragging rights (and prizes!).
Silent and live auction bidding will take place before Trivia begins, between rounds, and after the final round.
Food and Drink
Details coming soon!
Why it matters
Our annual Trivia Night & Auction allows the PTO to fund:
- Staff Grants
- Support a Cougar student needs
- Free Family Fun Nights (Bingo for Books & Glow Party)
- Staff Appreciation Meals & Gifts
- Charitable Gifts
- Community Service Events
- And more!
This event directly impacts every student and staff member at OTE.
Frequently Asked Questions
What is a Trivia Night?
A trivia night is an event where participants gather to answer questions across various categories in a competitive format. Teams write down their answers each round, and the team with the most correct answers wins!
Where is the event located?
The Cougar Classic Trivia Night & Auction will be held at Rosehill Winery in the Rosehill Gardens Event Space.
Address: 311 E. 135th St., Kansas City, MO 64145
The venue is located just east of 135th Street and State Line in Martin City.
This year’s event will be held outdoors under a tent. The tent will have side flaps to help keep in heat, and heaters will be running. However, April evenings can be unpredictable! If you tend to get chilly, we recommend dressing in layers and bringing a blanket to stay cozy while you play trivia.
What’s the theme?
The Cougar Classic is a golf-inspired trivia night with a fun Masters-weekend vibe — think Masters tradition + Caddyshack humor + Happy Gilmore energy. The theme sets the tone, but trivia is general knowledge (not golf-specific).
Do I need to know anything about golf to come?
Nope. Golf is the backdrop — the game is trivia. If you can bring random knowledge and a competitive streak, you’re ready.
Is there a dress code?
Golf-inspired attire is encouraged but totally optional. Come dressed up or come comfortable — you’ll fit right in.
What should I wear if I want to lean into the theme?
Anything from “tournament weekend” to “golf movie icon,” like:
- polos, quarter-zips, sundresses, skirts
- visors, bucket hats, fun sunglasses
- Masters green accents
- loud golf pants / bold patterns
- caddy outfits
- Happy Gilmore / Caddyshack inspired looks (keep it tasteful)
Does my team need to be only from OTE?
No! Invite whomever you’d like — neighbors, grandparents, friends from other schools, co-workers, etc.
This is an adults-only event, so please leave children at home.
What if I don’t have a team?
Register as an individual for $40/person and join one of our Community Tables. We will pair you with other individual registrants to form a team!
How many rounds of Trivia will there be?
10 rounds of 10 questions each, covering a wide array of categories.
What if I can’t attend — can I still bid?
Most silent auction items will be available for online bidding.
Live auction items will be available to in-person attendees only.
Can I get a refund if I can no longer attend?
Due to the logistics involved in planning this event, the PTO is unable to refund tickets or table purchases after March 28, 2026.
Registered Teams
The competition is heating up! 🔥 Here are the teams currently registered for The Cougar Classic:
🏆 Team Tables
🍎 Teacher Tables
🤝 Community Tables
Individual registrants will be grouped together to form Community Teams. Community team names will be announced the week of the event!
Questions? Email trivia@otepto.org.
