A shoutout to Jakyra S. for making this upgrade.
| Year | Mens Tourney | Womens Tourney | ||
|---|---|---|---|---|
| Team | Contestant | Team | Contestant | |
| 2026 | Michigan | James Wilkes | UCLA | Jakyra Simmons |
| 2025 | Florida | Charlie Carruth | Connecticut | Stephen Martin |
| 2024 | Connecticut | Eric Marland | South Carolina | Chris McRae |
| 2023 | Connecticut | Zach Andrews | LSU | Eric Marland |
| 2022 | Kansas | Zach Andrews | South Carolina | Caleb Lee |
| 2021 | Baylor | Mitch Parry | Stanford | Ethan Fenwick |
| 2020 | COVID-19 cancelled March Madness :( | |||
| 2019 | Virginia | Cindy Norris | Baylor | Joel Sanqui |
| 2018 | Villanova | Cindy Norris | Notre Dame | Eric Marland |
| 2017 | UNC | Barack Obama (as entered by JayF) | South Carolina | Alice McRae |
| 2016 | Villanova | Joel Sanqui | Connecticut | Eric Marland |
| 2015 | Duke | Adam Reagan | Connecticut | Stephen Bonawitz |
| 2014 | Connecticut | Charlie Carruth | Connecticut | Stephen Bonawitz |
| 2013 | Louisville | Daniel Burgner | Connecticut | Jean DeHart |
| 2012 | Kentucky | Chris McRae | Baylor | Eric Marland |
| 2011 | Connecticut | Ray Russell | Texas A&M | Alice McRae |
| 2010 | Duke | Jean DeHart | Connecticut | Stephen Bonawitz |
| 2009 | UNC | Rick Klima | ||
| 2008 | Kansas | Charlie Carruth | ||
| 2007 | Florida | Jay Fenwick | ||
| 2006 | Florida | Teeter McKnight | ||
| 2005 | UNC | Eric Marland | ||
| 2004 | Connecticut | Stephen Bonawitz | ||
| 2003 | Syracuse | Alice McRae | ||
| 2002 | Maryland | Darryl Cook | ||
| 2001 | Duke | Andrew Hostetler | ||
| 2000 | Michigan State | Ray Russell | ||
| 1999 | Connecticut | Charlie Carruth | ||
| 1998 | Kentucky | Theresa Early | ||
| 1997 | Arizona | Dee Parks | ||