Challenge the Coaches - Connor and Leilani

About this event

Think you've got solid pickleball technique? Prove it under pressure.

Challenge the Coaches pits you and a small group against professional pickleball coaches playing at full intensity — no easing up, no soft-serving. The coaches will come at you with pace, spin, and pinpoint placement, forcing you to execute real shots in real match conditions.

This isn't a technique clinic where you drill in a vacuum. It's live-fire training. Every dink, drop, reset, and drive you've been working on gets tested against players who will hit it hard at your body or place it exactly where it's toughest to reach — and you'll have to respond with clean, controlled technique anyway.

By the end of the session, you won't just know the right technique — you'll have proven you can execute it against players who are actively trying to break it down.

Event details

Challenge the Coaches - Connor and Leilani is a program hosted by Pickleball Clubhouse in Chicago, Illinois. It is listed as Special Instruction. The venue is at 4242 North Elston Avenue, Chicago, Illinois 60618. The next session starts on Wednesday, November 4, 2026 at 12:00 PM and ends at 1:00 PM, local time at the club. Sessions continue until November 18, 2026. Registration costs $40 USD. 2 of 6 spots are open. Players can register online as guests, without a Pickleball Clubhouse account. Pickleball Clubhouse has 12 courts for pickleball.

Location

Pickleball Clubhouse