Ultimate Pickleball Challenge serves up competition and community, June 27

Get ready to rally and compete when Madison College hosts Dream Doubles: The Ultimate Pickleball Challenge on Saturday, June 27, at Pickleball Kingdom in Sun Prairie.

The high-energy event welcomes alumni, friends, students and pickleball enthusiasts of all skill levels for a full day of friendly competition, interactive games and community connection from 9 a.m. to 2 p.m.

At the center of the action are the interactive Gold Medal Challenges — a signature experience featuring creative drills, mini-games and skill contests designed to test players’ speed, accuracy and strategy. Participants will earn a commemorative gold medal, plus prizes and bragging rights.

Developed in partnership with the UW Credit Union Basecamp Fitness, the Madison College Fitness Center, Madison College Fitness & Wellness Program students and the Capital Area Pickleball Association, the challenges range from trick shots to precision lobs and reaction-based competitions.

Adding excitement to the courts are appearances by former Wisconsin Badgers Roy Boone and Mike Iglinski, Robert Smith, “Mr. Basketball” Nimrod Hilliard and Madison College Wolfpack athletes.

Choose your challenge

•    Beginner’s Social | 9 a.m. – 11:30 a.m.| Free
Guided play, skill-building sessions and easygoing games for pickleball newcomers.
•    Gold Medal Challenge | 9 a.m. – 11:30 a.m. | Free
Fun for all ages and skill levels, the challenge features 10 skill stations and mini-games. Complete all 10 and earn a medal!
•    Intermediate Scramble | 12 – 2 p.m. | Players rated 3.0–3.8 | $20
•    Advanced Scramble | 12 – 2 p.m. | Players rated 3.8+ | $20
DUPR-rated pickleball players can register for the Intermediate or Advanced Division scramble. Medals will be awarded to round-robin competition winners, and all registered scramble players will receive an event T-shirt.

Play to support a good cause

Proceeds from tournament fees and court sponsorships help reduce financial barriers for Madison College students.

“Dream Doubles is about more than competition — it’s about bringing people together for an unforgettable experience that supports student success and strengthens community connections,” said Dr. Jimmy Cheffen, Madison College Director of Student Engagement and Community Impact.

Join the excitement and be part of an unforgettable day on and off the court. Register and learn more on the Madison College event webpage.