Comparison

Side Out vs Pickleball Drills

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

Head to head
About

Side Out

Effortlessly track pickleball scores directly from your Apple Watch with intuitive swipe gestures. This app manages serving order, player positions, and game statistics, allowing you to focus on playing. An optional companion scoreboard can be used on your iPhone or iPad for spectators.

Highlights
  • Hands-free Apple Watch scoring
  • Automatic serving order tracking
  • Companion iPhone/iPad scoreboard
  • Multiple game and scoring formats
  • Player profiles and performance tracking
  • Match history and stats
  • HealthKit integration
Features
Read full description

Track Pickleball scores hands-free on your Apple Watch. Simple swipes keep score while you play—no phone fumbling. See scores, serving order, and player positions at a glance. PERFECT FOR APPLE WATCH • Swipe up/down to score points—keep your phone in your bag • Automatic serving order tracking (no mental math!) • Green indicator shows current server and service box (1 or 2) • Undo/redo with simple swipes—fix mistakes instantly • Works independently on Watch—no iPhone needed during play SMART SCORING FEATURES • Doubles & Singles support • Multiple games per match tracking • Customizable winning score (with win-by-2 rule) • Auto-save & crash recovery—never lose your game • Player profiles to track performance over time • Side-out, Rally, and Simple scoring formats COMPANION SCOREBOARD • Use your iPhone/iPad as a live scoreboard for spectators • Voice announcements in proper Pickleball format (4-2-1) • Perfect for tournaments and casual play • Share scores with nearby players via Bluetooth MATCH HISTORY & STATS • Review past games and performance • Track wins/losses against opponents • iCloud sync across all your devices • HealthKit integration logs workouts automatically Whether you're playing casual rec games or competitive tournaments, Side Out makes scorekeeping effortless so you can focus on your game.

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+)

Screenshots

Side Out4 screens
Pickleball Drills4 screens

Verdict

The call

The clearest difference is in-app purchases: Side Out at none against Pickleball Drills's 3. Side Out also leads on ads (none vs shown). Pickleball Drills's advantage is rating (4.8 vs 4.5) and update cadence (every 6 days vs fortnightly). On price, review sentiment, 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. Side Out asks for nothing beyond the download.

ReceptionRating · Positive reviews · Number of ratings

Pickleball Drills holds the better App Store score, 4.8 against 4.5. Both are backed by a comparable volume of ratings — 82 and 303 respectively. Written reviews complicate that: 90% of Side Out's written reviews are positive against 87% of Pickleball Drills's, so the app with the better star average is not the one people write more warmly about.

UpkeepUpdate frequency

Side Out ships an update fortnightly, Pickleball Drills every 6 days. The most recent releases landed on September 10, 2026 and September 20, 2026 respectively.

Scorecard6 real differences · 4 level
Side Out versus Pickleball Drills: the parameters behind the verdict, then further details
ParameterSide OutPickleball Drills
PriceFreeFree
Rating4.5 (82 ratings)4.8 (303 ratings) — better
Positive reviews90.2% of reviews — better87.1% of reviews
Number of ratings82303 — better
Update frequencyFortnightlyEvery 6 days — better
AdsNo — betterYes
In-app purchasesNo — betterYes
MonetizationFree — betterSubscription
DevicesiPhone, iPad, Apple Watch — betteriPhone, iPad
Requires iOS17.016.0.2 — better
Further details — not scored
Size15 MB172 MB
Age rating4+4+
Developer205L StudioPickleball Playbook LLC

Customer experience

Side Out

All ratings82 ratings
Positive87.8%
Neutral7.3%
Negative4.9%
Written reviews61 reviews
Positive90.2%
Neutral3.3%
Negative6.6%

Pickleball Drills

All ratings303 ratings
Positive95.0%
Neutral1.0%
Negative4.0%
Written reviews132 reviews
Positive87.1%
Neutral1.5%
Negative11.4%

User reviews

Side Out

From 82 App Store ratings

What we love

  • 👍 Easy to use
  • 🚀 Fluid app performance
  • 💡 Fully customizable rules
  • 👍 Uncomplicated and works
  • 👍 Syncs to watch

Room to improve

  • 🐛 Not intuitive swipes
  • 🐛 Watch crown rotation issues
  • 🐛 Player name input greyed out
  • 🐛 App closes randomly on watch
  • 🐛 Workout app integration clunky

Pickleball Drills

From 303 App Store ratings

What we love

  • 🚀 Awesome drills
  • 👍 Easy to find & incorporate drills
  • 👍 Great drills and instructions
  • 👍 Helpful for improving game
  • 👍 Organized well and easy to use

Room to improve

  • 🐛 Scheduler does not work
  • 🐛 Login issues and app not working
  • 🐛 Billing and cancellation problems
  • 💡 Need more strategy-focused content
  • 🔒 No captions for deaf/hard of hearing players

Bugs and requests

Side Out

Reported bugs

13 issues
  • App on watch randomly closes and deletes match
  • Server switching courts not working
  • Undo is sometimes buggy
  • Display hangs occasionally
  • Not properly syncing app data from iPhone to watch
Show 8 more
  • Unable to begin a game on iPhone app
  • Unable to edit player data on iPhone app
  • Paid app froze and won't reinstall
  • Purchased app not on phone
  • App freezes during use
  • Accidentally awarding final point goes to 'Finish' screen
  • SE watch doesn't wake right away
  • Creating multiple Apple workouts when changing teams

Requested features

38 requests
  • Tennis app or section
  • Set up on phone, control on watch
  • In-game timer
  • Disable Watch crown rotation
  • Microphone control for player names
Show 33 more
  • Long press to replace names
  • Default setup option
  • Win/loss summary for all players
  • Change background color (black/white)
  • Use app with workout app for display priority
  • Save matches by sessions
  • Flip player view
  • Rally score option with 2 services
  • Archive feature
  • Stats against added players
  • Landscape mode for players
  • Add 'Myself' to either team
  • Exit and save option
  • Share scoreboard to another iPad
  • Games won under each player
  • Heart rate on Apple Watch version
  • Donation option
  • Play again with same team members
  • Disable crown for scoring
  • Error override feature
  • Delete players
  • Sync code for other players' watches
  • Quick start with option to add myself
  • Add players after QuickStart
  • Coin toss option
  • Time out option with timer
  • Save data to cloud and export
  • Track player errors
  • Track skinny/regular singles games
  • Program team side switching frequency
  • Summarize games played or export data
  • Confirmation or undo at end of game
  • Consolidate multiple Apple workouts

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

In-app purchases

None

Side Out

No 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

Questions

Is Side Out free?
Side Out is free to download, with no in-app purchases.
Is Pickleball Drills free?
Pickleball Drills is free to download, with in-app purchases available.
Which has better reviews, Side Out or Pickleball Drills?
Pickleball Drills is rated higher. Side Out averages 4.5 out of 5 from 82 ratings, while Pickleball Drills averages 4.8 from 303 ratings.
Do Side Out or Pickleball Drills have ads?
Pickleball Drills shows ads; Side Out does not.
Which is updated more often, Side Out or Pickleball Drills?
Side Out ships an update fortnightly, and Pickleball Drills every 6 days. Most recently, Side Out was updated on September 10, 2026 and Pickleball Drills on September 20, 2026.

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