Office Pool Software Compared: Free vs Paid (2026)

Every group has that one person who runs the pool. They print the grid, chase down the guy in accounting who still owes for his three squares, and text everybody the winners at halftime. If that person is you, you already know the spreadsheet-and-group-text method falls apart the second your pool gets bigger than about twelve people.

Office pool software fixes most of that. The question is which one, and whether you should pay for it. I run pools, I've poked around all the popular tools, and the honest answer is that the "best" one depends on what you're running and how much you care about spending money. So here's a straight comparison, warts and all.

The six tools worth knowing

There are a lot of pool sites out there, but six keep coming up when people search for office pool software: PickMySquare (that's us, I'll be upfront about the bias), EasyOfficePools, RunYourPool, SqMGR, SuperBowlSquares.org, and PrintYourBrackets.com. They don't all do the same thing, which is the part most comparison posts skip.

EasyOfficePools, SqMGR, and SuperBowlSquares.org are squares-focused, but they land in different price tiers: EasyOfficePools and SqMGR are free, SuperBowlSquares.org is paid by the grid. RunYourPool is the one broad platform that does squares, brackets, pick'em, and survivor, and prices accordingly. PrintYourBrackets.com covers the widest range of pool and bracket types on this list and hosts a live version of its squares grid for free, though its March Madness bracket tool looks more like a single-player fill-in-and-share page than a scored pool. Here's the quick version:

Now the part a table can't tell you: what each one actually feels like to use.

PickMySquare: free, and built for people who don't want a manual

I'll get our own pitch out of the way fast. PickMySquare is free, both products, no "free up to X and then we get you" catch. You make a squares board for any game with a score (NFL Sunday, an NBA night, the Frozen Four, whatever), share a link, and people claim squares from their phones without making an account. Numbers auto-draw, winners get flagged live, done.

We also run bracket pools, but only for one thing: NCAA March Madness, men's and women's. That's the whole tournament bracket format. We don't do NFL survivor or weekly pick'em, and I'd rather tell you that now than have you sign up expecting it. If squares plus March Madness brackets covers your group, this is the cheapest good option, because it costs nothing.

The tradeoff is ads. The site runs them, and that's the deal that keeps it free for a board of thirty people instead of charging your commissioner. If you've never run a board before, the beginner's guide to football squares walks through it in about five minutes.

EasyOfficePools: genuinely easy, but the free tier is tiny

EasyOfficePools earns its name. You can set up a football squares board in seconds, no account, share a public URL, and let people pick. For a small group it's clean and quick.

The catch is the free line sits low. Your pool is free with four or fewer entries, and once you pass that it's $5 for one game. Four entries is small. If everybody at your office grabs squares, you're at ten, fifteen, twenty entries in a hurry, and now every game is another five bucks. For a one-off Super Bowl board that's nothing. For someone running a board every Sunday all season, it adds up in a way that's easy to not notice until you look. It isn't football-only, either: EasyOfficePools also runs March Madness (basketball) squares, Kentucky Derby boards, and a custom squares option for other events.

RunYourPool: the everything platform, if you'll pay for it

RunYourPool is the most feature-loaded name on this list and the most expensive. It runs squares, brackets, pick'em, confidence pools, survivor pools, all of it, and it does them well. Pricing scales with how many entries you have, so check their calculator for the exact cost at your pool size.

If your group runs multiple pool types across the year (a survivor pool in the fall, a bracket in March, squares for the big games), one paid platform that handles everything is a reasonable call. You get no ads and a polished experience because you're footing the bill. For a single squares board or a casual March Madness bracket, though, you're paying for a lot of machinery you won't touch. Know what you actually need before you buy the whole suite.

SqMGR: free, focused, and a little bare

SqMGR deserves more attention than it gets. It's a free, no-ads squares manager for football and basketball, run by a small open-source team. No account needed to play, custom colors, live scoring, shareable links. If your only goal is a clean squares grid and you dislike ads, it's a legitimately good pick.

Where it stops is scope. It's squares and nothing else, so no brackets, no pick'em. It's also a smaller operation, which means the polish and the support aren't at the level of the paid tools. For a lot of people that's a fine trade for free and quiet.

SuperBowlSquares.org: the priciest option, but you're buying real depth

SuperBowlSquares.org is the one tool here you pay for by the grid, not by the entry or the season. A single-game or Super Bowl grid runs $25, a full NFL regular season grid runs $35, and buying more than one gets you a volume discount (10% off 2 to 10 grids, up to 25% off 50 or more). There's no free tier. Creating a grid means buying one.

What that price buys is real breadth. The platform explicitly supports college football, NBA, and March Madness squares on top of NFL and the Super Bowl, all with automatic winner tracking tied to live scores, password-protected grids, and QR code sharing. Players don't need an account to join someone's grid, they enter a code for that specific pool, so the cost and the setup work land on the person running it, not the group. It's built well for fundraisers specifically too: several of the site's own sample grids split the pot 50/50 between a charity and the winning squares.

If you're comparing purely on price, this is the expensive one on the list. If you want a platform with two decades behind it and don't mind paying for that, it's a real alternative to the free tools here.

PrintYourBrackets.com: hosts squares for free, but the bracket tool doesn't score itself

PrintYourBrackets' football squares tool hosts a live pool online for free, not just a printable one. Share it by QR code, the grid fills in as people claim squares, and it includes its own random number generator for the digit draw. Cost per square is an optional field you set for your own group's buy-in, not a platform fee. The page doesn't say whether "Live Updates" means the winning square updates itself from real game scores or just shows the grid filling up live, and it doesn't state an account requirement either way, so treat both as open questions rather than settled facts.

March Madness gets a separate tool. Their interactive bracket lets you click your own pick to win each game and share the finished bracket by a unique link, but nothing on that page mentions a leaderboard or standings comparing multiple people's picks. PrintYourBrackets does run a real hosted product with an automated, tracked leaderboard (no logins needed, you join and type a display name), but that's their separate NFL weekly pick'em tool, not the NCAA bracket. If you want a scored, ranked bracket pool the way PickMySquare or RunYourPool run one, that combination isn't confirmed for March Madness on this site.

Beyond football and basketball, the platform also generates brackets for pretty much any sport or activity, up to 128 teams, cornhole included, plus pick'em and confidence pool formats. Its other business is physical products: poster-size boards and scratch-off cards, sold through its own store and a companion site, scratchsquares.com.

If what you want is a squares grid, printed or hosted, this is a genuinely strong free option. If you want the pool scored and ranked for you the way PickMySquare or RunYourPool do it, only some of PrintYourBrackets' tools are confirmed to do that, and the March Madness bracket isn't one of them.

So which one should you actually use?

Depends on the pool.

Running squares for the Super Bowl or a single playoff game with a normal-sized group? Any of the free options works, and you'll pick based on ads versus features. Running boards all season across different sports? A free tool that handles any sport saves you the per-game charges that quietly pile up elsewhere. Need survivor and confidence pools on top of squares? Pay for RunYourPool and stop reading comparison posts. Want SuperBowlSquares.org's two-decade feature set and don't mind paying by the grid? That tradeoff is what it's built for. Just want a squares grid without paying, printed or hosted online? PrintYourBrackets covers both: print it and pass it around, or share it by QR code and let the group claim squares live.

The mistake I see most is people paying for a heavy platform to run one Super Bowl board, or picking a tool with a four-entry free cap for a thirty-person office. Match the tool to the pool. And if you want to understand the game itself before you pick a host, the football squares strategy guide covers which numbers actually matter once the grid fills in.

Office pool software FAQ

What's the best free office pool software?
For squares across any sport plus March Madness brackets, PickMySquare is free with no entry cap. SqMGR is a strong free squares-only option if you want no ads. EasyOfficePools is free too, but only up to four entries before it charges per game. PrintYourBrackets.com is also free, both its printable grids and its hosted online squares pool.

Is PickMySquare really free, or is there a catch?
Both products (squares boards and NCAA bracket pools) are free with no per-game or per-entry fee. The site runs ads, and that's what pays for it instead of charging the person running the pool.

Can I run a March Madness bracket pool on these tools?
PickMySquare and RunYourPool both do NCAA bracket pools with a live leaderboard. EasyOfficePools, SqMGR, and SuperBowlSquares.org don't offer bracket pools at all. PrintYourBrackets.com has both a printable bracket and an online one you fill in and share by link, but nothing on its bracket pages mentions a leaderboard ranking multiple people's picks against each other, so a scored group contest isn't confirmed there. If you want a bracket, check out our March Madness bracket pool guide.

Do my pool members have to create accounts?
On PickMySquare, EasyOfficePools, and SqMGR, people can join and pick without making an account. RunYourPool generally has participants sign in. SuperBowlSquares.org uses an entry code per grid instead of a player account. PrintYourBrackets.com doesn't state an account requirement for its squares pool either way, though its separate NFL pick'em tool is explicitly no-login (join and type a name). For an office group that just wants to grab squares fast, the confirmed no-account tools remove a lot of friction.

What does RunYourPool cost?
Pricing scales with the number of entries and the pool type you're running. Check their pricing calculator for your exact setup.

What does SuperBowlSquares.org cost?
It's priced per grid, not per entry: $25 for a single-game or Super Bowl grid, $35 for a full NFL regular season grid, with volume discounts starting at two grids. There's no free tier.

Can I run squares for basketball or hockey, not just football?
On PickMySquare, yes, a squares board works for any game with a score, so NBA, NHL, and college games all work. SqMGR supports football and basketball. EasyOfficePools does football, basketball (March Madness), and Kentucky Derby squares. SuperBowlSquares.org covers NBA and March Madness squares alongside football. PrintYourBrackets.com's squares tool is football-focused.