Winners of the annual Gross match play tournament
Jackson Park Men’s Club Champions
| 2020 | Jay Clark | 1990 | Ken Jenson |
| 2019 | Mark Ohrenschall | 1989 | Chris Robinson |
| 2018 | Joe Zucker | 1988 | Dale Hanowell |
| 2017 | Joe Zucker | 1987 | Nace Powell |
| 2016 | Mark Ohrenschall | 1986 | Chris DeGrazia |
| 2015 | Mark Ohrenschall | 1985 | Dale Hanowell |
| 2014 | Mark Ohrenschall | 1984 | Dale Hanowell |
| 2013 | Jeff Schoening | 1983 | Butch Manolides |
| 2012 | Aaron Mackey | 1982 | Steve Storey |
| 2011 | Scott Furrow | 1981 | Chris DeGrazia |
| 2010 | Matt Remington | 1980 | Ed Pearsall |
| 2009 | Chris Gray | 1979 | Paul Koenig |
| 2008 | Ian Courtnage | 1978 | Mike O’Laughlin |
| 2007 | Trevor Cameron | 1977 | Ed Pearsall |
| 2006 | Trevor Cameron | 1976 | Mike O’Laughlin |
| 2005 | Matt Steele | 1975 | Ed Pearsall |
| 2004 | Jon Moscrip | 1974 | Gordy Price |
| 2003 | Ken Jenson | 1973 | Ed Pearsall |
| 2002 | Ken Jenson | 1972 | Ed Pearsall |
| 2001 | Chris DeGrazia | 1971 | NONE |
| 2000 | Chris DeGrazia | 1970 | John Rawlings III |
| 1999 | Chris DeGrazia | 1969 | John Rawlings III |
| 1998 | Ken Jenson | 1968 | John Tuft |
| 1997 | Ken Jenson | 1967 | John Tuft |
| 1996 | Ken Jenson | 1966 | Ernie Tullis |
| 1995 | Ken Jenson | 1965 | Ed Pearsall |
| 1994 | Ken Jenson | 1964 | Dan Scott |
| 1993 | Ken Jenson | 1963 | Dan Scott |
| 1992 | Ken Jenson | 1962 | Wayne McDaniels |
| 1991 | Ken Jenson | 1961 | Bill Tindall |
| 1960 | Bill Tindall | ||
| 1959 | Ralph Sullivan | ||
| 1958 | Frank Marolich | ||
| 1957 | Bill Conroy | ||
| 1956 | Bill Conroy | ||
| 1955 | Bill Conroy |