CHRONICLE OF THE CONTEST:

It started on a shabby poster-board in a dormitory hallway. Twenty-three years ago in upstate South Carolina, a few friends started a small March Madness bracket contest available for anyone on campus who wanted to join. We only had 41 participants that first year.

The tournament began to gain more and more traction in subsequent years as advertising dollars increased and sponsors began coming in. Dunkin Donuts was a faithful sponsor of the modest NCAA Contest in those early years. The tournament intensified to 121 contestants during my senior year in 2002. With the advancement of the World Wide Web and the remarkable assistance of New England friends like Lucas Lampman and Matt Taylor, the NCAA Contest continued to grow in the 2000’s. The number of contestants has steadily increased over the past decade and is positioned for unrelenting expansion thanks to your faithful participation. We added more ‘sponsors’ in 2019 to truly position this contest for broader reach to expose more basketball fans to opportunities to pour themselves out. As we enter 2023, the PYO Challenge has found itself alongside ESPN, Yahoo, Fox Sports, and USA Today as one of the largest Free March Madness contests in the country as rated by several outlets in recent years. Article. Article. Thank you for making this a special contest!

Some past highlights:

  • In 2003, Paul Dickerson won by a jaw-dropping 138 points and still holds the all-time largest margin of victory.

  • In 2009, Matt Dodge selected 53 out of 63 games correctly, including a perfect elite eight, final four, finals, and champion. Matt still holds the highest point total in PYO Challenge history at 981.

  • In 2014 we had our youngest winner, Luke Bush (age 6), ride an implausible Kentucky team to victory.

  • In 2022, Andrew Straka, from Cleveland, Ohio, won it all with 691 points defeating 941 formidable challengers.

I sincerely delight in hosting this tournament to facilitate someone’s One Shining Moment!

Collection of Past Winners: