Comparison

Pickleball Drills vs Courtside

Price, ratings, monetisation and update history for both apps, side by side — with what reviewers say about each.

Head to head
About

Pickleball Drills

Enhance your pickleball skills with daily drills and video instruction. Access a library of routines for all levels, including solo options for home or court practice. Improve your dinks, drops, volleys, and more with expert guidance.

Highlights
  • Daily pickleball drills
  • Video instruction for each drill
  • Drills for all skill levels
  • Solo practice drills (wall/ball machine)
  • Improve dinks, drops, and volleys
  • Monthly new drill uploads
Features
Read full description

The Pickleball Drills App by Pickleball Playbook is designed to help you improve your game every single day, no matter your level. With new drills uploaded monthly and videos for each drill, you’ll have the ability to work on what you want, when you want. No partner to drill with? No problem. We’ve got you covered with wall drills you can do at home, or ball machine drills you can do on the court. Gone are the days of wondering what drill to do to help you improve your dinks, drops, drives, volleys, and more. HOW TO JOIN & ACCESS THE PICKLEBALL DRILLS APP Download the App and subscribe to the Pro Membership or Basic Membership for unlimited access to all trainings and drills. PERKS Join the private Facebook group. Here you will get access to exclusive giveaways, trainings, and pickleball tips. DRILLS Each drill will take 30 to 60 minutes and will provide players with repetition & the mental skills needed for match play. Each drill includes video instruction and pro tips from some of the best players in the world! FEATURES "Drop" into trainings that help you improve your game every day, every day, every day, including the following: Beginner (1.0-3.49) Intermediate (3.5-4.49) Advanced (4.5+)

About

Courtside

This app connects pickleball organizers with players, simplifying event creation, management, and real-time scoring. Discover local games, join events, and track match results seamlessly. It handles all the administrative tasks so participants can focus on playing.

Highlights
  • Create and publish pickleball events
  • Manage player rosters and waitlists
  • Run live scoring and court assignments
  • Seed and run tournament brackets
  • Discover local pickleball events
  • Track live scores and match results
  • View player statistics
Features
Read full description

Courtside connects the people who organize pickleball with the people who show up to play — one app for both sides of the net. FOR ORGANIZERS • Create and publish events in minutes: courts, capacity, tournament format, and start time • Keep events in draft while you plan, then flip them live when you're ready • Manage your roster — see who's joined, who's waitlisted, and invite your followers directly • Run live scoring on game day: enter scores, track rounds, and manage court assignments in real time • Seed and run brackets across round robin, single elimination, double elimination, Swiss, and group stage formats FOR PLAYERS • Discover pickleball events and communities near you by location and radius • Follow the organizers and clubs you trust — their events land right in your feed • Join open events in one tap, or land on the waitlist if a game is full • Track live scores and match results as they happen, court by court • View player stats — wins, losses, and win rate — for anyone in an event Courtside handles the logistics that usually live in group chats, spreadsheets, and side conversations — so clubs can spend their energy on the game, not the admin.

Screenshots

Pickleball Drills4 screens
Courtside4 screens

Verdict

The call

The clearest difference is in-app purchases: Courtside at none against Pickleball Drills's 3. Courtside also leads on ads (none vs shown). Pickleball Drills's advantage is ratings volume (312 vs 2) and update cadence (every 6 days vs every 3 weeks). On price, rating, device support and iOS requirement there is nothing between them.

Scored on Price · Rating · Positive reviews · Number of ratings · Update frequency · Ads · In-app purchases · Monetization · Best chart rank · Devices · Requires iOS

CostPrice · In-app purchases · Ads · Monetization

Both are free to download. Pickleball Drills sells 3 in-app purchases, starting at $19.99 per month. Courtside asks for nothing beyond the download.

ReceptionRating · Positive reviews · Number of ratings

Courtside holds the better App Store score, 5.0 against 4.8. That said, the two scores are not equally well evidenced: Pickleball Drills has 312 ratings behind it against 2, so its average is the more settled of the two.

UpkeepUpdate frequency

Pickleball Drills ships an update every 6 days, Courtside every 3 weeks. The most recent releases landed on November 3, 2026 and October 31, 2026 respectively.

Scorecard5 real differences · 5 level
Pickleball Drills versus Courtside: the parameters behind the verdict, then further details
ParameterPickleball DrillsCourtside
PriceFreeFree
Rating4.8 (312 ratings)5.0 (2 ratings) — better
Positive reviews87.2% of reviews—
Number of ratings312 — better2
Update frequencyEvery 6 days — betterEvery 3 weeks
AdsYesNo — better
In-app purchasesYesNo — better
MonetizationSubscriptionFree — better
DevicesiPhone, iPad — betteriPhone
Requires iOS16.0.2 — better16.4
Further details — not scored
Size172 MB54 MB
Age rating4+12+
DeveloperPickleball Playbook LLCInfralogics, LLC

Customer experience

Pickleball Drills

All ratings303 ratings
Positive95.0%
Neutral1.0%
Negative4.0%
Written reviews141 reviews
Positive87.2%
Neutral1.4%
Negative11.3%

Courtside

All ratings2 ratings
Positive100.0%
Neutral0.0%
Negative0.0%

Bugs and requests

Pickleball Drills

Reported bugs

3 issues
  • Scheduler does not work
  • Login issues and app not working
  • Billing and cancellation problems

Requested features

2 requests
  • Dark mode option
  • More strategy-focused content

Courtside

Not enough reviews yet to summarise bugs or requests.

In-app purchases

3 purchases

Pickleball Drills

Subscriptions3
  • Monthly Subscription7 Days trial$19.991 Month
  • Biannual Subscription7 Days trial$89.996 Months
  • Annual Subscription7 Days trial$149.991 Year
None

Courtside

No in-app purchases

Questions

Is Pickleball Drills free?
Pickleball Drills is free to download, with in-app purchases available.
Is Courtside free?
Courtside is free to download, with no in-app purchases.
Which has better reviews, Pickleball Drills or Courtside?
Courtside is rated higher. Pickleball Drills averages 4.8 out of 5 from 312 ratings, while Courtside averages 5.0 from 2 ratings.
Do Pickleball Drills or Courtside have ads?
Pickleball Drills shows ads; Courtside does not.
Which is updated more often, Pickleball Drills or Courtside?
Pickleball Drills ships an update every 6 days, and Courtside every 3 weeks. Most recently, Pickleball Drills was updated on November 3, 2026 and Courtside on October 31, 2026.

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