Given to honor the Junior tennis player who has won the Boys Singles for three years in a row.
In 2017, the award was renamed for Tommy Voekler, son of Marty and Jenny Voeker.
|1981||Toby Halsey||(John Totolis Trophy Retired)|
|1982||Bill Halsey||1996||Cyrus Philbrick|
|1983||Frank Conley||1997-98||David Andrias|
|1984-86||John Totolis||1999||Cyrus Philbrick|
|(Roger Rowe Trophy Retired)||2000-02||William Heyniger|
|1987-88||James A. McGee||(William Heyniger Trophy Retired)|
|1989-90||Whit Townsend||2014-17||Tommy Voelker|
|1991-92||Grant Stuart||2018||Finn McMillan|
|1993-95||John Heyniger||2019||Not held|