| Singles | Doubles |
1986 | – | – |
1987 | – | – |
1988 | – | – |
1989 | – | – |
1990 | – | – |
1991 | Dan Ritschel (65th-96th) | – |
1992 | Dan Ritschel (65th-96th) | – |
1993 | Dan Ritschel (33rd-48th) | Aaron Zobrist/Matt Dowling (65th-96th) |
1994 | – | – |
1995 | – | – |
1996 | – | – |
1997 | – | Daren Gravlin / Jon Vanecko (33rd-48th) |
1998 | – | Andy Gravlin / Blake Stewart (97th-128th) |
1999 | – | Chris Marchand / Jason Vanecko (97th-128th) |
2000 | – | Andy Gravlin / Chad Whittington (65th-96th) |
2001 | Andy Gravlin (49th-64th) | Ty Wyffels / Kyle Shoff (97th-128th) |
2002 | Ty Wyffels (65th-96th) Tony Winkler (97th-128th) | Kyle Shoff / Joe Harris (25th-32nd) |
2003 | Ty Wyffels (65th-96th) | Kyle Shoff / Joe Harris (33rd-48th) Andy Ngo / Andy Laird (65th – 96th) |
2004 | John Armstrong (97th-128th) | Kyle Shoff / Nate Rauh (17th-24th) Nick Vaughn / Mike Axelson (65th – 96th) |
2005 | Nate Rauh (33rd-48th) Nick Vaughn (97th – 128th) | John Armstrong / Mike Axelson (33rd-48th) |
2006 | – | Nick Vaughn / Tyler Lampe (25th-32nd) |
2007 | Ryan Donnelly (97th-128th) | Stephan Rauh / Tyler Lampe (33rd-48th) David Stewart / Nate Wilson (65th – 96th) |
2008 | Stephan Rauh (33rd-48th) Ryan Donnelly (65th – 96th) | David Stewart / Tyler Lampe (65th-96th) Nate Wilson / Matt Elliott (97th – 128th) |
2009 | – | David Stewart / Stephan Rauh (13th-16th) Greg Coffman / Jared Rauh (97th – 128th) |
2010 | Stephan Rauh (13th-16th) Kevin Wang (65th – 96th) | David Stewart / Nate Wilson (13th-16th) Greg Coffman / Ryan Donnelly (65th – 96th) |
2011 | Will Koehrsen (25th-32nd) Petr Vesely (33rd-48th) | Mitchell Nguyen / Quinn Vaughn (49th-64th) Christoph Goettler / Tyler Ngo (65th-96th) |
2012 | Will Koehrsen (25th-32nd) Mitchell Nguyen (49th-64th) | Christoph Goettler / Quinn Vaughn (17th-24th) |
2013 | Mitchell Nguyen (49th-64th) | Christoph Goettler / Will Koehrsen (6th) |
2014 | Will Koehrsen (9th-12th) Mitchell Nguyen (33rd-48th) | Ryan Willard / Fletcher Koehrsen (65th-96th) (Trevor Lewandowski sub for injured Willard) |
2015 | – | Ryan Willard / Fletcher Koehrsen (25th-32nd) Brendan Axelson / Joel Sutter (97th-128th) |
2016 | – | Ryan Willard / Fletcher Koehrsen (17th-24th) Brendan Axelson / Carsten Boast (33rd-48th) |
2017 | – | Fletcher Koehrsen / Carsten Boast (3rd) Johan Olsen / Ethan Greenfield (17th-24th) |
2018 | Michael Poppen (25th-32nd) Brian Lelm (49th-64th) | Ethan Greenfield / Grant Gutwein (17th-24th) Keegan DeShon / Zack Lambiase (49th-64th) |
2019 | Ethan Greenfield (17th-24th) Cullen Nevitt (33rd-48th) | Michael Poppen / Brian Lelm (13th-16th) Joey Shallat / Brett Manwaring (49th-64th) |
2020 | Season Cancelled by IHSA | Season Cancelled by IHSA |
2021 | Bryton Short (17th-24th) Alexander Schroff (49th-64th) | Brian Lelm / Harry Hawbaker (2nd) Keagan Nevitt / Griffin Hammond (17th-24th) |
2022 | Alexander Schroff (25th-32nd) Hudson Shaw (49th-64th) | Nate Geurink / Griffin Hammond (33rd-48th) Cole Morris / Mason Walker (49th-64th) |
2023 | Bryton Short (9th-12th) Alexander Schroff (33rd-48th) | Hudson Shaw / Dane Hutchison (33rd-48th) |