2023 Winsidr Bracket Challenge

The women’s college hoops regular season has wrapped up, and it’s tourney time. Spring is around the corner, upsets are brewing, and the madness is creeping in. After a successful first run last year that saw 264 participants in our first-ever Winsidr Bracket Challenge, we’re running it back. 

And this year, we’re doing it bigger, partnered up with WNBA vet Erica McCall to bring some more competition to the ranks! Can you best her and the entirety of the Winsidr staff?

Sure, our team can talk our trash internally on the Winsidr Slack, but we want to see what y’all think. Are Aliyah Boston and the undefeated Gamecocks going to run the table and become back-to-back champs, or can someone from the field knock them from their throne? While South Carolina has yet to take an L, it takes just one stumble in March to fall short of the ultimate goal. Maybe you’re pulling for one of the PAC-12 powerhouses in Stanford and Utah, or you believe that Caitlin Clark’s Hawkeyes can outshoot every opponent they see, or you think UConn can put together a string of healthy games for the first time this season. In March, upsets abound.


So, let’s get into this. Entry is totally FREE, and we’ve got some great prizes for the top competitors.

Do you think you know more about NCAAW than the Winsidr team? Come and prove it! Whether this is your first time filling out a bracket or you’re a tourney vet, it’s easy to play! 


Here’s a quick refresher on the rules:

You can make your selections however you see fit: by ranking favorite players or school associations, by tabulating strength of record against conference difficulty, by rating cutest mascots, or a thousand other ways. All that matters is when the first jump ball is airborne, you’ve filled out a complete bracket.

We have created a pool over at ESPN. It’s private to our group, so you’ll need to fill in the group name and password, listed below:

Group name: Winsidr Bracket Challenge
Password: draftlottery


As of Sunday night, the field is set, but it’s important to note that the first game tips off this Friday, March 17, at 11:30 a.m. ET, so you need to have your picks in before then! As for how this all works, the rules are simple:

  • You go through each matchup, one at a time, and click on the team you think will win. That little “i” icon gives you information about the matchup, such as record and stats. There are a few play-in games, so there won’t be info on those that look like (11) Dayton/(11) DePaul because the field of 64 technically hasn’t been completely set yet. Don’t fret, though! Those qualifiers that get us from 68 to 64 teams are not a part of our pool, so they don’t affect when our picks lock.

  • Upsets count as double, so be sure to pick some! Any time a higher seed beats a lower seed, you get twice as many points for that round (even a 9 over an 8). 
  • Each subsequent round doubles in points. For example, a win in the opening round gives you one point for a win, two for an upset. Round two awards two points for a win, four for an upset, and this continues to escalate all the way through to the championship game.
  • You make ALL your picks at the beginning, not as you go. This includes a score tiebreaker for the title game. The brackets lock ahead of the first matchup on Friday.


While bragging rights hold their own currency—and you should absolutely let us have it on social media once you’ve got us beat—we are also awarding the top performers with some physical prizes. Thanks to our generous affiliates, we’ve got some really cool rewards for players that finish in the top three.

See Also

A couple of quick shoutouts to two companies that are helping to gear up our winners! Homage’s line of WNBA logo shirts (of franchises new and old!) are an absolute must for W fans. And if you’ve been buying WNBA merch for years, you likely already know about the gear over at BreakingT, which are some of the most unique and personalized sports products on the market.

Even if you don’t hit the reward tier, please support these companies that are out there raising the profile of the W with their hard work. By using the affiliate links below, you’re also helping us out at Winsidr. 

Homage link: homage.sjv.io/Winsidr23
BreakingT Link: BreakingT.com/winsidr


Okay, on to the freebies! At this point, we’re revealing three prizes, but there will be more surprises added to the list by the time the tourney tips off on Friday.

First place: one tee from the Winsidr Shop, a $150 gift card to Homage, and a League Pass subscription
Second place: one tee from the Winsidr Shop, two tees *or* a hoodie from BreakingT
Third place: one tee from the Winsidr Shop

So, pencil in your favorites, channel your Cinderellas, and secure some swag. Be sure to share your results across social media using the hashtag #WinsidrBracket to keep the conversation going with all your Winsidr favorites. 

And get ready for madness.

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