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 four tools worth knowing

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

Two of them are squares-focused. One is a broad platform that does everything. And one is a free, open-source squares tool run by a small team. 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.

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.

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.

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. EasyOfficePools and SqMGR don't offer bracket pools. 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. For an office group that just wants to grab squares fast, the 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.

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.