The coach

Dylan Dean

My passion for racket sports began around age eight, when I first picked up a tennis racket. Throughout my tennis career I qualified for state competitions multiple times, building a competitive foundation that carried over into pickleball.

I discovered pickleball while recovering from medical challenges and quickly fell in love with the sport, its competitive nature, and the community around it.

Over the past two years I've developed into a competitive 5.0+ player and have coached more than 100 players across every skill level, from complete beginners to drilling and playing practice matches with Kaitlyn Christian, one of the world's top women's singles players.

In August 2026 I earned my Professional Pickleball Registry (PPR) Level 1 Certified Professional certification. Through Dyl Pickle, my goal is to make high-quality coaching accessible at every stage. Whether you're picking up a paddle for the first time or preparing for tournament play, I want to help you build confidence, improve your skills, and understand the game more deeply.

Dylan hitting a forehand on an outdoor court at night

By the numbers

On the court

100+Players coached
5.0+Competitive level
2Years playing pickleball
L1PPR Certified Professional

Certified

PPR Level 1 Professional

Certified by the Professional Pickleball Registry, earned in Chicago in August 2026. Valid August 2026 through August 2027.

PPR certificate naming Dylan Dean a Level 1 Certified Professional, valid August 2026 to August 2027

The journey

The road here

From tennis courts to the kitchen line.

  1. Age 8

    First racket

    Picked up tennis and went on to qualify for state competitions multiple times.

  2. 2024

    Found pickleball

    Discovered the sport while recovering from medical challenges and fell for it fast.

  3. 2025

    Started coaching

    Began teaching players of every level, from first-timers up.

  4. Aug 2026

    PPR certified

    Earned PPR Level 1 Certified Professional in Chicago.

  5. 2026

    LUZZ sponsorship

    Partnered with LUZZ as a sponsored pickleball athlete and coach.

  6. Today

    Dyl Pickle

    Competing at the 5.0+ level and coaching 100+ players in Springfield.

Gallery

Booking

Your next session starts here

Pick a program, a location, and a time. Sessions at The Pickle & Chilly Dill are paid at the court.