The WIAA goes back to 1925 to determine the beginning of its boys tennis tournament program. Tournaments reportedly were held as early as 1919, but no records are available prior to 1925.

Shorewood won the team championship (as well as singles and doubles titles) in 1925 when the tournament was held at the University of Wisconsin in Madison.

The tournament continued at UW-Madison through 1931, then was held at Neenah through 1940. In the next 30 years, the site rotated among a half-dozen sites (Nicolet in Glendale held about a third of the tournaments). Nielsen Stadium (indoors) became the site of the State Tournament in 1973, and it has been held at that site since that time.

Nicolet leads in number of State team championships with 26 (one a tie), including eight in a row from 1967-74. Neenah is a distant second in team titles with 10 (one tie). Marquette has eight team titles, while University School of Milwaukee is next on the list with seven. Manitowoc (one tie) and Whitefish Bay have six. Six of University School of Milwaukee's seven titles came consecutively from 2006-2011. Shorewood (one tie) and Milwaukee Washington (two ties) are next with four State titles won.

In 1995, a two-division format was adopted for boys tennis, which also included a separate team tournament series based on dual meet competition. Neenah captured the first Division 1 team title in the new format, beating Brookfield Central 4-3. Greendale won the first Division 2 team title by beating Brown Deer 5-2. Singles and doubles were contested in two divisions in a separate tournament.

John Whitlinger of Neenah (1969-72) and Marc Eisen of Nicolet (1986-89) are the only two players to win four State singles championships. Bill Reed of Shawano (1939-41), Charles Bleckinger of Oshkosh (1959-61), Mark Loughrin of Greendale (1992, 1994-95), Eric Robertson of Nicolet (1996, 1998-99) and Michael Dierberger of Nicolet (2004-06) won three State singles titles. There have been 13 others who have won two singles titles. The tandem of Erich Palecek and Kevin Caiati of Greendale is the only doubles team to win three straight championships, and there have been only seven tandems that have won two straight titles with the same two persons both years. Four other boys have won doubles championships two years with different partners.

Nicolet boys have won the singles championship 16 times. Oshkosh, Marquette and Milwaukee Washington boys have won seven times, and singles players from Neenah and Shorewood have won six titles. Nicolet pairs have won 15 doubles titles. Neenah is next with 12, and Manitowoc and Shorewood duos are third with six doubles crowns.